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171596-29-5

Basic Information
CAS No.: 171596-29-5
Name: Cialis
Molecular Structure:
Molecular Structure of 171596-29-5 (Cialis)
Formula: C22H19N3O4
Molecular Weight: 389.40
Synonyms: Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-;(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;GF 196960;Tadalafil [USAN];Tildenafil;Calais;(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;Adcirca;
EINECS: 200-835-2
Density: 1.51 g/cm3
Melting Point: 298-300 °C
Boiling Point: 679.1 °C at 760 mmHg
Flash Point: 364.5 °C
Solubility:
Appearance: white to off-white cyrstalline solid
Hazard Symbols: F,Xn
Risk Codes: 11-20/21/22-36
Safety: 16-36/37
Transport Information:
PSA: 74.87000
LogP: 2.08710
Synthetic route

C22H19ClN2O5*(x)ClH

74-89-5

methylamine

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%
74-89-5

methylamine

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

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

74-95-3

1,2-dibromomethane

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%
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

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%
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

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
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

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%
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

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

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

74-89-5

methylamine

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%
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

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%
120-57-0

piperonal

C15H19N3O3*ClH

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%
74-89-5

methylamine

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

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

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%
474668-76-3

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

52605-49-9

sarcosine ethyl ester hydrochloride

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%
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

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;
120-57-0

piperonal

5241-64-5

Boc-D-Trp-OH

79-04-9

chloroacetyl chloride

74-89-5

methylamine

A

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

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%
120-57-0

piperonal

rhodaninoic acid

rhodaninoic acid

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
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
171596-41-1

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

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

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

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
120-57-0

piperonal

glycocoll ester

glycocoll ester

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
4299-70-1, 7303-49-3, 22032-65-1

D-Tryptophan methyl ester

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
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

593-51-1

methylamine hydrochloride

A

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

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;
120-57-0

piperonal

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
120-57-0

piperonal

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

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

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
120-57-0

piperonal

1422164-52-0

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

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
5241-64-5

Boc-D-Trp-OH

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
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

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%
81-04-9

naphthalene-1,5-disulfonate

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

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

salicylic acid

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

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

(S)-Mandelic acid

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

Conditions
ConditionsYield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;94.25%
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

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%
141-82-2

malonic acid

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

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;
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

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;
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

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

4-Methoxybenzenethiol

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

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

2-Fluoro-5-nitropyridine

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

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 40h; Inert atmosphere;61%
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

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

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

Conditions
ConditionsYield
With [(Tp)NiIV(CF3)3] In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;43%
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

Conditions
ConditionsYield
With tert.-butylnitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 15h; Irradiation;42%
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

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
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

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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Chemistry

The Molecular Structure of Tadalafil (CAS NO.171596-29-5):

Empirical Formula: C22H19N3O4
Molecular Weight: 389.404 
Appearance:  Off-White Cyrstalline Solid
Nominal Mass: 389 Da
Average Mass: 389.404 Da
Monoisotopic Mass: 389.137556 Da 
Index of Refraction: 1.758
Molar Refractivity: 105.27 cm3
Molar Volume: 256.2 cm3
Surface Tension: 81.5 dyne/cm
Density: 1.51 g/cm3
Flash Point: 364.5 °C
Enthalpy of Vaporization: 99.67 kJ/mol
Boiling Point: 679.1 °C at 760 mmHg
Vapour Pressure: 2.67E-18 mmHg at 25°C 
Melting Point: 298-300°C
Product Categories: Active Pharmaceutical Ingredients;Cnbio;Erectile Dysfunction;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's
InChI: InChI=1/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
Smiles: C1N(C([C@H]2Cc3c([C@H](N2C1=O)c1ccc2c(c1)OCO2)[nH]c1ccccc31)=O)C

History

 Tadalafil (CAS NO.171596-29-5) was discovered by Glaxo Wellcome (now GlaxoSmithKline) under a partnership between Glaxo and ICOS to develop new drugs that began in August 1991. In December 2003, after sildenafil (Viagra) and vardenafil (Levitra),the Food and Drug Administration approved tadalafil (as Cialis) for sale in the United States as the third ED prescription drug pill. Then in May 2009,Tadalafil  was approved  in the United States for the treatment of pulmonary arterial hypertension and is currently under regulatory review in other regions for this condition.

Uses

 Tadalafil (CAS NO.171596-29-5) can be used for the treatment of erectile dysfunction under the name Cialis. Recently Tadalafil  (CAS NO.171596-29-5) has been approved for the treatment of pulmonary arterial hypertension and other onditions.

Safety Profile

The most common side effects of tadalafil are: are headache, indigestion, flushing,back pain, muscle aches and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen), these usually go away after a few hours. Back pain and muscle aches maybe occur 12 to 24 hours after taking the drug,and the symptom usually disappears after 48 hours.

Specification

 Tadalafil  (CAS NO.171596-29-5) is the main raw materials of Cialis,compare with Sildenafil,Tadalafil have less side effects, after taking two days,30% of people have muscles ache feeling (mainly waist and legs). It is also called as Tadalafil [USAN] ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (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 ; Adcirca ; Cialis ; Tadalafil ; Tadalafil Lilly ;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)- ; Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)- .