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Cialis tadalafil CAS 171596-29-5
Cas No: 171596-29-5
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Tadalafil or Tadanafil powder
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High Purity Sex powder Tadanafil Powder Tadalafil Tablets for ED CAS 171596-29-5
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High purity Tadalafil Male Sex Hormones 99%
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Bosang Tadanafil powder CAS NO.171596-29-5 99% White solid
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Tadalafil/ CAS No.171596-29-5
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Qualification Cialis tadanafil CAS no. 171596-29-5 IC351 GF-196960X
Cas No: 171596-29-5
USD $ 9.2-9.2 / Kilogram 1 Kilogram 20 Metric Ton/Month Hebei youze Biotechnology Co.,Ltd Contact Supplier

171596-29-5 Usage

Warnings and precautions

Patients currently taking nitrates, experiencing angina pectoris, suffering from heart disease, patients who have unregulated hypertension or hypotension, or patients who have had a stroke in the past 6 months should not take Cialis.

Side effects

Adverse effects related to oral therapy for erectile function are primarily concerned with adverse cardiovascular effects, because PDE5 inhibitors promote vasodilation and, therefore, have an inherent potential to cause hypotension. This is a particular concern for elderly patients with a preexisting condition.

Description

Tadalafil (market name “Cialis” or “Adcirca”) is a kind of PDE5 inhibitor used for the treatment of erectile dysfunction, benign prostatic hypertrophy and pulmonary arterial hypertension. The effect of Tadalafil is relaxing the blood vessels muscles and increasing the blood flow into the corpus cavernosum. The mechanism of action of tadalafil is through inhibiting the activity of the cGMP specific phosphodiesterase type 5 (PDE5). PDE5 degrades cGMP in the corpus cavernosum located around the penis. Therefore, tadalafi leads to the increased concentration of cGMP which further causes the smooth muscle relaxation and increased blood flow into the corpus cavernosum. Some clinical studies also implied that tadalafil could improve endothelia function in men with increased cardiovascular risk and lower the urinary tract symptoms secondary to benign prostatic hyperplasia.

Uses

analgesic, norepinephrine uptake blocker, mu-opiod receptor agonist.A phosphodiesterase 5 inhibitor.

Chemical Synthesis

D-(-)-Tryptophan methyl ester (175) and 1,3- benzodioxole-5-carboxaldehyde (176) were subjected to a modified Pictet-Spengler reaction to form cis- and transtetrahydro- β-carboline tricyclic compounds. The ciscompound 177 was isolated as a white solid in 42% yield. The basic nitrogen in the piperidine ring of 177 was acylated with chloroacetyl chloride (179) to give compound 180 in 93% yield. Finally, the diketonepiperazine ring was formed by adding 180 to 33% methylamine in ethanol under refluxing conditions and yielded tadalafil (XXII) in 77% as a white solid.

Pharmacokinetics

Tadalafil is different in structure from both sildenafil and vardenafil. It is rapidly absorbed and peaks in concentration (378 μg/L after a 20-mg dose) after 2 hours, displaying a long half-life of 17.5 hours. It also is metabolized by the liver (CYP3A4). Notably, its pharmacokinetics is not clinically influenced by alcohol or food intake or by factors such as diabetes or impaired hepatic or renal function.

References

https://www.drugs.com/tadalafil.html https://www.drugbank.ca/drugs/DB00820 Roehrborn, C. G., et al. "Tadalafil administered once daily for lower urinary tract symptoms secondary to benign prostatic hyperplasia: a dose finding study." Journal of Urology 180.4(2008):1228. Rosano, Giuseppe M. C., et al. "Chronic Treatment with Tadalafil Improves Endothelial Function in Men with Increased Cardiovascular Risk." European Urology 47.2(2005):214-222.

Clinical Use

Tadalafil is one of the two new PDE5 inhibitors launched for the oral treatment of male erectile dysfunction. Tadalafil is a b-carboline derivative and it is structurally distinct from vardenafil (Levitraw) and sildenafil (Viagraw), both of which are PDE5 inhibitors based on a fused pyrimidine core structure. Tadalafil is synthesized in three steps starting from D-tryptophan methyl ester, by first condensing with piperonal in a Pictet-Spengler cyclization reaction to form the tetrahydro-β-carboline derivative, which is followed by chloroacetylation of the piperidine ring nitrogen and cyclization with methylamine. Tadalafil is a potent and highly selective inhibitor of PDE5 (IC50=1 nm). It shows >10,000-fold selectivity for PDE5 versus PDE1, 2, 3, 4, 7, 8 and 9, and >700-fold selectivity versus PDE6. Typically administered at 10 and 20 mg doses, tadalafil is rapidly absorbed and has a tmax of 2 h, which is slightly longer than those of sildenafil (1 h) and vardenafil (0.75 h). Clinically, all of these agents appear to have efficacy for many men within 30–60 min. However, tadalafil distinguishes itself from other PDE5 inhibitors in terms of significantly longer duration of action. The half-life of tadalafil dosed at 20 mg is 17.5 h as compared with 3.8 h for sildenafil (100 mg) and 4.7 h for vardenafil (20 mg). In clinical studies, significant rates of response were reported up to 36 h following drug ingestion. Tadalafil is predominantly metabolized in the liver by CYP3A4 to entities that are not active against PDE5 and excreted mainly as metabolites in the feces and the urine. The pharmacokinetics of tadalafil are unaffected by factors such as intake of food and alcohol, age, the presence of diabetes, and mild or moderate hepatic insufficiency. The most common drug-related adverse events are headache, back pain, dyspepsia, and myalgia. At 10 and 20 mg doses, Tadalafil does not have a significant effect on blood pressure and heart rate and does not result in increased instances of myocardial infarction. Rare reports of prolonged erections greater than 4 h and priapism have been noted with the use of tadalafil. Priapism, if not treated properly, can result in irreversible damage to the erectile tissue. Patients who have an erection lasting greater than 4 h are advised to seek emergency medical attention. Tadalafil has a modest synergistic effect on the nitrate-induced reduction in blood pressure and, as with sildenafil and vardenafil, it is contraindicated for use in patients on nitrate therapy. In diabetic patients, improvement of erectile function by tadalafil is irrespective of the type of diabetes and the type of diabetic therapy.

Indications and uses

Cialis (or Tadalafil) was developed by American pharmaceutical company Lilly. It is used to treat erectile dysfunction and belongs to a second generation of PDE5 inhibitors. Studies show that Cialis works very quickly, taking effect in around 15-20 minutes, and has a prolonged effect that can last for up to 36 hours. T1/2 is 17.5h.

Chemical Properties

White to Off-White Cyrstalline Solid

Definition

ChEBI: A pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione substituted at position 2 by a methyl group and at position 6 by a 1,3-benzodioxol-5-yl group (the 6R,12aR

Mechanism of action

Tadalafil was the last agent to be released and can be taken on a full stomach without slowing the onset. It has a much longer duration of action, lasting up to 48 hours, compared with sildenafil and vardenafil, which last for approximately 4 hours. The longer half-life of tadalafil results in a lengthened period of responsiveness as compared to sildenafil and vardenafil. This longer therapeutic window requires fewer time constraints for the effectiveness of tadalafil and has been interpreted as being advantageous through providing the option for more spontaneous sexual activity. Because of its long half-life, however, tadalafil, has been detected in plasma even 5 days after oral administration. This suggests the possibility of accumulation if taken regularly and in short intervals, which may result in an increased risk of side effects with the excessive use of this PDE5 inhibitor. The 3,4-methylenedioxy substitution on the phenyl ring was significant for increasing its potency as PDE5 inhibitor. Optimization of the chain on the piperazinedione ring resulted in no significant change in IC50s. Tadalafil is a highly potent PDE5 inhibitor (IC50, 5 nM), with high selectivity for PDE5 versus PDE1 through PDE4. The PDE5/PDE6 selectivity ratio is 85.

Originator

Lilly/ICOS (US)

General Description

Tadalafil, (6R-trans)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1', 2' :1,6]pyrido[3,4-b]indole-1,4-dione (Cialis), is a potent PDE5 inhibitor.It received FDA approval for the treatment of erectiledysfunction in December 2003. Because of its half-life of17.5 hours, it is marketed as a 36-hour treatment. Tadalafil ispredominantly metabolized by hepatic enzymes, includingCYP3A4. The concomitant use of CYP3A4 inhibitors suchas ritonavir, indinavir, ketoconazole, as well as moderateCYP3A inhibitors such as erythromycin have been shown toresult in significant increases in tadalafil plasma levels.Much like sildenafil, tadalafil is under clinical investigationfor managing PAH.

Side effects

No severe negative reactions. No perceived facial flushing or sight abnormalities following medication. Rare cases of headache and indigestion.

Brand name

Cialis (Lilly).

Clinical Research

In a study of 348 cases of mild to severe erectile dysfunction, patients were randomly given 20mg of Cialis or a placebo. Results showed that in comparison to the placebo group, patients who took Cialis experienced improved intercourse success in the 24-36 hours following medication, with many patients achieving successful sexual intercourse twice in 36 hours. Side effect rate and severity were also no different from those of the placebo group. Over 5% of patients in the Cialis group experienced headaches and indigestion.
InChI:InChI=1/C22H23N3O3/c1-24-8-9-25-17(22(24)26)11-15-14-4-2-3-5-16(14)23-20(15)21(25)13-6-7-18-19(10-13)28-12-27-18/h2-7,10,15,17,20-21,23H,8-9,11-12H2,1H3/t15?,17-,20?,21-/m1/s1

171596-29-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (Y0001417)  Tadalafil  European Pharmacopoeia (EP) Reference Standard 171596-29-5 Y0001417 1,880.19CNY Detail

171596-29-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Tildenafil

1.2 Other means of identification

Product number -
Other names Cialis

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:171596-29-5 SDS

171596-29-5Synthetic route

C22H19ClN2O5*(x)ClH

C22H19ClN2O5*(x)ClH

methylamine
74-89-5

methylamine

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In dichloromethane at 0 - 5℃; for 3h; Temperature; Solvent;99.3%
methylamine
74-89-5

methylamine

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃;95%
In N,N-dimethyl-formamide at 20℃; for 10h;95%
In methanol for 3h; Reflux; Large scale;95.3%
(6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione

1,2-dibromomethane
74-95-3

1,2-dibromomethane

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 6h;95%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;93%
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
1224724-00-8

(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With hydrogen; Raney Ni In ISOPROPYLAMIDE at 80℃; under 2280.15 Torr; for 22h; Product distribution / selectivity;94%
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With methylamine In dichloromethane for 2h;93.5%
With methylamine In water for 20h; Ionic liquid;355 mg
sarcosine ethyl ester hydrochloride
52605-49-9

sarcosine ethyl ester hydrochloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With potassium carbonate In ethylene glycol at 110℃; Solvent; Reagent/catalyst; Temperature; Green chemistry;92.7%
1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
749864-18-4

1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 20℃; for 1h;92%
C22H20N4O3

C22H20N4O3

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Stage #1: C22H20N4O3 With sulfuric acid In isopropyl alcohol for 12h; Reflux;
Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h; Temperature;
91.2%
(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

methylamine
74-89-5

methylamine

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In tetrahydrofuran; water at 50℃; Solvent; Temperature;91%
sarcosine
107-97-1

sarcosine

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Stage #1: sarcosine; (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride With triethylamine In tetrahydrofuran at 30℃; for 0.333333h;
Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Solvent; Reagent/catalyst; Temperature; Further stages;
90.54%
piperonal
120-57-0

piperonal

C15H19N3O3*ClH

C15H19N3O3*ClH

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In isopropyl alcohol at 80℃; for 16h; Solvent; Temperature;58.2%
methylamine
74-89-5

methylamine

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

A

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-27-3

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

B

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In methanol at 50℃; for 16h;A 1.1%
B 54%
(1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid hydrochloride
474668-76-3

(1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid hydrochloride

sarcosine ethyl ester hydrochloride
52605-49-9

sarcosine ethyl ester hydrochloride

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 50 - 55℃; for 10h; Large scale reaction;52.6%
(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide
951661-81-7

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Stage #1: (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -50 - -35℃; for 2 - 6h;
Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate at -40 - 30℃; Product distribution / selectivity;
48%
Stage #1: (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide With n-butyllithium In tetrahydrofuran; hexane at -40 - -35℃; for 2.5h;
Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate at -40 - 30℃; Product distribution / selectivity;
piperonal
120-57-0

piperonal

Boc-D-Trp-OH
5241-64-5

Boc-D-Trp-OH

chloroacetyl chloride
79-04-9

chloroacetyl chloride

methylamine
74-89-5

methylamine

A

(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione
171596-28-4

(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione

B

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Stage #1: Boc-D-Trp-OH With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Microwave irradiation;
Stage #2: piperonal With trifluoroacetic acid In chloroform for 0.5h; Pictet-Spengler cyclisation; Microwave irradiation;
Stage #3: chloroacetyl chloride; methylamine Further stages;
A 45%
B 32%
piperonal
120-57-0

piperonal

rhodaninoic acid

rhodaninoic acid

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C
2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C
3: 54 percent / methanol / 16 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / aq.HCl / methanol / 36 h / Heating
2: 78 percent / NaHCO3 / CH2Cl2; H2O
3: 88 percent / CHCl3; ethanol / 7 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h
2: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C
3: 92 percent / methanol / 16 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h
2: DMAP; basic alumina / CH2Cl2 / 2 h / -25 - 20 °C
3: 92 percent / piperidine / dimethylformamide / 1 h / 20 °C
View Scheme
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C
2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C
3: 54 percent / methanol / 16 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / aq.HCl / methanol / 36 h / Heating
2: 78 percent / NaHCO3 / CH2Cl2; H2O
3: 88 percent / CHCl3; ethanol / 7 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h
2: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C
3: 92 percent / methanol / 16 h / 50 °C
View Scheme
(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
171596-41-1

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C
2: 54 percent / methanol / 16 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: 93 percent / NaHCO3 / CHCl3 / 20 °C
2: 77 percent / ethanol / Heating
View Scheme
(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / NaHCO3 / CH2Cl2; H2O
2: 88 percent / CHCl3; ethanol / 7 h / Heating
View Scheme
(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C
2: 92 percent / methanol / 16 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: DMAP; basic alumina / CH2Cl2 / 2 h / -25 - 20 °C
2: 92 percent / piperidine / dimethylformamide / 1 h / 20 °C
View Scheme
piperonal
120-57-0

piperonal

glycocoll ester

glycocoll ester

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
3: 77 percent / ethanol / Heating
View Scheme
D-Tryptophan methyl ester
4299-70-1, 7303-49-3, 22032-65-1

D-Tryptophan methyl ester

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
3: 77 percent / ethanol / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water; toluene / 15 h / Reflux; Large scale
2.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Large scale
2.2: 1 h / 20 °C / Large scale
3.1: methanol / 3 h / Reflux; Large scale
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / 10 h / 70 - 80 °C / Large scale
2: triethylamine / chloroform / 2 h / 20 - 30 °C
3: methylamine / dichloromethane / 2 h
View Scheme
methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
1321600-91-2

methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

methylamine hydrochloride
593-51-1

methylamine hydrochloride

A

(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione
171596-28-4

(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione

B

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With triethylamine In methanol Reflux;
piperonal
120-57-0

piperonal

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 3 h / 85 °C
1.2: 1 h / 0 - 10 °C
2.1: water; tetrahydrofuran / 1 h / 55 °C / Inert atmosphere
View Scheme
piperonal
120-57-0

piperonal

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.25 h / 110 °C
2: triethylamine / water; tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere
3: water; tetrahydrofuran / 1 h / 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 0.25 h / 110 °C
2: triethylamine / tetrahydrofuran; water / 2 h / 0 - 10 °C / Inert atmosphere
3: tetrahydrofuran; water / 1 h / 55 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: acetonitrile / 105 °C / Autoclave
2: sodium carbonate / acetonitrile; water / 5 - 10 °C
3: water; isopropyl alcohol / 110 - 120 °C
View Scheme
N-Boc-D-tryptophan

N-Boc-D-tryptophan

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / Inert atmosphere
1.2: 1 h / -20 - 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C
3.1: toluene / 8 h / 110 °C
View Scheme
C24H25N3O5

C24H25N3O5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
In toluene at 110℃; for 8h;0.39 g
piperonal
120-57-0

piperonal

(R)-ethyl 2-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)-N-methylpropanamido)acetate
1422164-52-0

(R)-ethyl 2-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)-N-methylpropanamido)acetate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C
2: toluene / 8 h / 110 °C
View Scheme
Boc-D-Trp-OH
5241-64-5

Boc-D-Trp-OH

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere
1.2: 0.5 h / -20 °C / Inert atmosphere
2.1: 4-methyl-morpholine / tetrahydrofuran / Inert atmosphere
2.2: 1 h / -20 - 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C
4.1: toluene / 8 h / 110 °C
View Scheme
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-27-3

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide; isopropyl alcohol at 83℃; for 5h;98%
naphthalene-1,5-disulfonate
81-04-9

naphthalene-1,5-disulfonate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione naphthalene-1,5-disulfonic acid salt

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione naphthalene-1,5-disulfonic acid salt

Conditions
ConditionsYield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;95.4%
salicylic acid
69-72-7

salicylic acid

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione salicylic acid salt

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione salicylic acid salt

Conditions
ConditionsYield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;94.81%
(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione mandelic acid salt

(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione mandelic acid salt

Conditions
ConditionsYield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;94.25%
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
1021702-43-1

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With water-d2; potassium carbonate In tetrahydrofuran; dimethylsulfoxide-d6 at 65℃; for 16h;94%
malonic acid
141-82-2

malonic acid

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

C3H4O4*C22H19N3O4
1242099-10-0

C3H4O4*C22H19N3O4

Conditions
ConditionsYield
In ethyl acetate for 5h;85%
In acetonitrile Product distribution / selectivity;
In acetonitrile at 25℃; for 0.5h;
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

3-((2-(benzo[d][1,3]dioxole-5-carbonyl)-1H-indol-3-yl)methyl)-1-methylpiperazine-2,5-dione
1220393-12-3

3-((2-(benzo[d][1,3]dioxole-5-carbonyl)-1H-indol-3-yl)methyl)-1-methylpiperazine-2,5-dione

Conditions
ConditionsYield
With dipotassium peroxodisulfate; water; tetramethlyammonium chloride In dimethyl sulfoxide at 40℃; for 7h;79%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; water at 20℃; for 8h; Product distribution / selectivity;
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

C22H19N3O5

C22H19N3O5

Conditions
ConditionsYield
With N-Bromosuccinimide; acetic acid at 50℃; for 5h; Reagent/catalyst;78%
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R)-6-(6-((4-methoxyphenyl)thio)benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

(6R)-6-(6-((4-methoxyphenyl)thio)benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction;65%
2-Fluoro-5-nitropyridine
456-24-6

2-Fluoro-5-nitropyridine

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-7-(5-nitropyridin-2-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-7-(5-nitropyridin-2-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 40h; Inert atmosphere;61%
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

C22H15(2)H4N3O4

C22H15(2)H4N3O4

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;46%
2,8-difluoro-5-(trifluoromethyl)-5Hdibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate

2,8-difluoro-5-(trifluoromethyl)-5Hdibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

C23H18F3N3O4

C23H18F3N3O4

Conditions
ConditionsYield
With [(Tp)NiIV(CF3)3] In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;43%
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

C22H19N3O5

C22H19N3O5

Conditions
ConditionsYield
With tert.-butylnitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 15h; Irradiation;42%
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione

11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione

Conditions
ConditionsYield
With potassium superoxide; 18-crown-6 ether In N,N-dimethyl-formamide at 25℃; for 6h; Winterfeldt oxidation;38%
Multi-step reaction with 2 steps
1: O2; KOtBu / dimethylformamide; tetrahydrofuran / 4 h
2: 16.2 mg / PyBrOP; di-isopropylethylamine / dimethylformamide; tetrahydrofuran / 16 h / 25 °C
View Scheme
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
171596-29-5

(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4-dithione
422311-80-6

(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4-dithione

Conditions
ConditionsYield
With Lawessons reagent In tetrahydrofuran at 20℃; for 72h;25%

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