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139755-83-2 Usage

Indications

Sildenafil (Viagra) was developed more than 10 years ago as an antihypertensive and antianginal drug. It proved ineffective in these applications but was shown to affect the smooth muscles of the penis.

Brand name

Viagra (Pfizer);Segurex.

Indications

Sildenafil (Viagra) is a selective inhibitor of PD-5, an enzyme that inactivates cGMP. Vardenifil (Levitra) is a particularly effective inhibitor of PD-5. It has a shorter onset of action and can be used in smaller doses than sildenafil. Other drugs used in the treatment of ED exert their effects through other biochemical pathways, both central and peripheral.

Indications and Usage

Sildenafil Citrate is an oral drug used to treat male erectile dysfunction and is a 5-phosphodiesterase inhibitor developed by the American Pfizer Pharmaceuticals to originally treat cardiovascular disease that was later discovered to improve patients’ sex lives. Sildenafil Citrate treats erectile dysfunction and was the first clinical oral drug used to specifically target male erectile dysfunction.

Uses

An orally active selective type 5 cGMP phosphodiesterase inhibitor.

Clinical Use

Sildenafil is a selective inhibitor of cGMP-specific PD-5 and therefore inhibits the degradation of cGMP. PD-5, the predominant type in the corpus cavernosum, also is present in other tissues (e.g., lungs, platelets, and eye). The selective inhibition of this enzyme facilitates the release of nitric oxide and smooth muscle relaxation of the corpus cavernosa. Sildenafil enhances erection by augmenting nitric oxide–mediated relaxation pathways. It has been suggested that sildenafil’s mechanism of action is due to cross-talk between cGMP- and cAMPdependent transduction pathways within the cavernous muscles.

Originator

Pfizer (UK)

Uses

Sildenafil, the first US FDA-approved, oral phosphodiesterase type-5 inhibitor, has revolutionized the treatment of erectile dysfunction sine its approval in 1998. Since sildenafil is a potent inhibitor of cyclic guanosine monophosphate in the corpus cavernosum and therefore increases the penile response to sexual stimulation.

Metabolism

In vitro metabolism studies for sildenafil have shown that the primary metabolite, N-desmethylsildenafil, and the minor metabolite, oxidative opening of the piperazine ring, are mediated by CYP3A4, CYP2C9, CYP2C19, and CYP2D6. The estimated relative contributions to clearance were 79% for CYP3A4, 20% for CYP2C9, and less than 2% for CYP2C19 and CYP2D6. These results demonstrate that CYP3A4 is the primary cytochrome mediating N-demethylation and that drugs inhibiting CYP3A4 likely impair sildenafil biotransformation and clearance. The pharmacokinetics of radiolabeled sildenafil were consistent with rapid absorption, first-pass metabolism, and primarily fecal elimination of N-demethylated metabolites. The absorption of sildenafil following oral administration was rapid (~92%), whereas the oral bioavailability was approximately 38% as a result of first-pass metabolism.

Uses

antiviral

Side effects

Orally administered sildenafil is an effective and well-tolerated treatment for men with ED, including those with diabetes mellitus. It has also been used for so-called salvage therapy in men who do not respond to intracorporeal injections of other agents. Headache is a common side effect, as are flushing and rhinitis.More serious side effects include definite or suspected myocardial infarctions and cardiac arrest.

Description

Sildenafil was launched as Viagra in the US for the treatment of organic orland psychological male erectile dysfunction (ED). Sildenafil can be obtained by functional rearrangement of the corresponding 5-aryl 1,3-dialkyl pyrazolo[4,3- d]pyrimidin-7-one, itself synthesized in a seven-step sequence from a pyrazole- 5-carboxylate. Sildenafil is a potent and selective inhibitor of type V cGMP phosphodiesterases (PDE5) ; IC50 = 3nM on isozymes from human corpus cavernosum tissue. This orally-active therapy is completely new and presents advantages over the classically recommended options such as vacuum constriction devices, drug injection or prosthesis implantation ; for these reasons, this first drug is likely to have a large acceptance fot the treatment of male ED. In experiments with incubated rabbit penile tissue, Sildenafil was shown to cause accumulation of cGMP. By inhibiting the enzyme PDE5, the predominant isozyme in the corpus cavernosum, Sildenafil induces an elevation of levels of second messager cGMP, which is involved in the regulation of vascular tone ; it was suggested that the specific elevation of cGMP due to Sildefanil would mediate an enhancement of nitric oxide-dependent relaxation of corpus cavernosal tissue. Several clinical studies using 10-100 mg Sildenafil have confirmed a good effectiveness and tolerability in healthy males. New trials in women with sexual disfunction have been initiated and positive results could enlarge the potential market of this drug.

Definition

ChEBI: A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.

Mechanism of action

Sildenafil is readily absorbed after oral administration and reaches peak plasma levels after about an hour. It undergoes hepatic metabolism and has a terminal half-life of about 4 hours.An initial dose of 50 mg is taken about an hour prior to sexual activity to induce penile erection.

Adverse Reactions

Common adverse reactions include headache, dizziness, facial flushing, indigestion, nasal congestion, and sight abnormalities, which may be expressed as difficulty differentiation blue/green colors, light sensitivity, or blurry vision. More severe adverse effects include decreased supine blood pressure and decreased cardiac output. Additionally, clinical research shows that engaging in sexual activity after taking Sildenafil Citrate increases the risk of heart abnormalities, including angina pectoris, dizziness, nausea, and other symptoms, and it may also cause sudden cardiac death.

Chemical Properties

White Solid

Manufacturing Process

A mixture of 3-n-propylpyrazole-5-carboxylic acid ethyl ester (24.1 g, 0.132 mol) (prepared by the method of Chem. Pharm. Bull., 1984, 32, 1568) and dimethyl sulfate (16.8 g, 0.133 mol) were heated to 90°C for 2.5 h. The mixture was dissolved in dichloromethane and the solution washed with sodium carbonate solution. The organic phase was separated, dried (MgSO4) and evaporated under vacuum to give a solid. Chromatography on silica gel (300 g), eluting with dichloromethane gave the 1-methyl-3-n-propylpyrazole- 5-carboxylic acid ethyl ester as a colourless oil (20.4 g, 79%).1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester (20.2 g, 0.10 mol) was suspended in 6 N aqueous sodium hydroxide solution (50 ml, 0.30 mol). The mixture was heated to 80°C for 2 h then diluted with water (50 ml) and acidified with concentrated hydrochloric acid (25 ml). Filtration gave the 1- methyl-3-n-propylpyrazole-5-carboxylic acid as pale brown crystals (12.3 g, 71%), melting point 150°-154°C.1-Methyl-3-n-propylpyrazole-5-carboxylic acid (12.1 g, 0.072 mol) was added portionwise to a mixture of oleum (13 ml) and fuming nitric acid (11 ml), keeping the temperature below 60°C. After the addition, the mixture was heated at 60°C overnight and then cooled to room temperature before being poured onto ice. Filtration of the precipitate gave the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxylic acid as a white solid (11.5 g, 75%), melting point 124°-127°C.1-Methyl-4-nitro-3-n-propylpyrazole-5-carboxylic acid (11.3 g, 0.053 mol) was added to thionyl chloride (50 ml) and the resulting mixture heated under reflux for 3 h. The reaction mixture was then cooled and excess thionyl chloride removed by evaporation under vacuum. The oily residue was dissolved in acetone (50 ml) and the solution cautiously added to a mixture of ice (50 g) and concentrated aqueous ammonium hydroxide solution (50 ml). The precipitate was collected by filtration to provide the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxamide as a pale yellow solid (8.77 g, 78%), melting point 141°-143°C.1-Methyl-4-nito-3-n-propylpyrazole-5-carboxamide (3.45 g, 16.2 mmol) and stannous chloride dihydrate (18.4 g, 81 mmol) were suspended in ethanol and the mixture heated under reflux for 2 h. The resulting solution was cooled to room temperature, basified to pH 9 by the addition of 2 N aqueous sodium hydroxide solution and extracted with dichloromethane (3 x 150 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum. Trituration of the residue with ether gave the 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide as an off-white solid (2.77 g, 94%), melting point 98°-101°C.A solution of 2-ethoxybenzoyl chloride (6.1 g, 33.0 mmol) in dichloromethane (50 ml) was added to a stirred solution of 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide (3.0 g, 16.4 mmol), 4-dimethylaminopyridine (0.02 g, 0.1 64 mmol) and triethylamine (3.34 g, 33.0 mmol) in dichloromethane (50 ml) at 0°C. The resulting mixture was allowed to warm to room temperature and stirred for a further 2 h. The solvent was evaporated under vacuum, the residue dissolved in a 19:1 mixture of dichloromethane and methanol (250 ml), and then the solution washed with 1 N hydrochloric acid (100 ml), dried (MgSO4) and evaporated under vacuum. The crude material was chromatographed on silica gel (200 g), eluting with a 97:3 mixture of dichloromethane and methanol, to give a pink solid; crystallisation from ethyl acetate-hexane gave the 4-(2-ethoxybenzamido)-1-methyl-3-npropylpyrazole- 5-carboxamide as a pale pink solid (2.2 g, 40%), melting point 153°-155°C.4-(2-Ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide (223 g, 0.676 mol) was added portionwise to a solution of sodium hydroxide (54 g, 1.35 mol) and 30% hydrogen peroxide solution (224 ml) in water (2000 ml). Ethanol (700 ml) was added and the resulting mixture heated under reflux for 2.5 h, cooled, then evaporated under vacuum. The resulting solid was treated with 2 N hydrochloric acid (380 ml), with external cooling, and the mixture was extracted with dichloromethane (1 x 700 ml, 3 x 200 ml). The combined organic extracts were washed successively with saturated aqueous sodium carbonate solution (3 x 400 ml) and brine (300 ml), then dried (Na2SO4) and evaporated under vacuum. Chromatography of the residue on silica gel (1000 g), using a methanol in dichloromethane elution gradient (0-1%), followed by trituration of the crude product with ether (300 ml), gave the 5-(2- ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a colourless solid (152.2 g, 72%), melting point 143°-146°C.5-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one (10.0 g, 32.1 mmol) was added portionwise to chlorosulfonic acid (20 ml) at 0°C under a nitrogen atmosphere. After being stirred overnight, the reaction solution was cautiously added to ice-water (150ml) and the aqueous mixture extracted with a 9:1 mixture of dichloromethane and methanol (4 x 100 ml). The combined extracts were dried (Na2SO4) and evaporated under vacuum to give the required 5-(5-chlorosulphonyl-2- ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a white solid (12.8 g, 97%), melting point 179°-181°C.4-Methylpiperidine was added to a stirred suspension of 5-(5-chlorosulphonyl- 2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one in ethanol at room temperature. The resulting mixture was stirred for 4 days before removing the solvent by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of dichloromethane and methanol and the solution washed with saturated aqueous sodium carbonate solution. The aqueous phase was further extracted with dichloromethane-methanol mixtures (3 x 100 ml) and all the organic fractions were combined, dried (MgSO4) and evaporated under vacuum to give a solid. Crystallisation from a mixture of methanol-dimethylformamide gave the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one as an off-white solid, melting point 187°- 189°C.After addition of citric acid to the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one (sildenafil) the it's salt is obtained, namely sildenafil citrate.

Enzyme inhibitor

Sildenafil is rapidly absorbed and peaks in concentration (127–560 ng/mL) after 0.5 to 2.0 hours, displaying a half-life of 3 to 4 hours for the full therapeutic dose (25–100 mg). It is 96% bound to plasma proteins and is metabolized by the liver CYP3A4. The metabolite N-desmethylsildenafil possesses approximately 50% of the activity of the parent molecule.

Therapeutic Function

Vasodilator
InChI:InChI=1/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)

139755-83-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name sildenafil

1.2 Other means of identification

Product number -
Other names SIDANAFIL

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:139755-83-2 SDS

139755-83-2Synthetic route

4-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
200575-15-1

4-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 120℃; for 0.166667h; Cyclization; microwave irradiation;100%
With potassium tert-butylate In tert-butyl alcohol for 8h; Reflux;44%
With sodium hydroxide In water for 8h; Reflux;280 mg
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With pyridine In water at 50℃; Reagent/catalyst; Temperature;93.9%
With triethylamine In methanol at 20℃; for 0.75h; Product distribution / selectivity;91%
In acetone at 20℃; for 3h; Sealed tube;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-methylpiperazine hydrochloride
34352-59-5, 50398-09-9, 51545-09-6

1-methylpiperazine hydrochloride

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With triethylamine; N-ethyl-N,N-diisopropylamine In water at 60℃; for 1.2h;91.8%
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-39-0

7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol at 90℃; for 1.5 - 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;
90%
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol for 2h; Reflux;
Stage #2: With hydrogenchloride In water pH=8.5 - 9.5; Product distribution / selectivity;
90%
With water for 4h; Product distribution / selectivity; Heating / reflux;83%
Stage #1: 7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With hydrogenchloride; water at 60℃; for 2h;
Stage #2: With sodium hydrogencarbonate In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;
79%
7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-54-9

7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine With water; sodium hydrogencarbonate In tert-butyl alcohol for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 0℃; pH=8.5 - 9.5; Product distribution / selectivity;
75%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
226956-42-9

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 1-methyl-piperazine; 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide In dichloromethane for 2h;
Stage #2: With potassium carbonate In isopropyl alcohol for 4h; Reagent/catalyst; Reflux;
71.7%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(2-ethoxy-5-iodophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
1491216-01-3

5-(2-ethoxy-5-iodophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-(2-ethoxy-5-iodophenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one With 1,10-Phenanthroline; potassium pyrosulfite; tetraethylammonium bromide; sodium formate; palladium diacetate; triphenylphosphine In dimethyl sulfoxide at 70℃; for 2h; Inert atmosphere; Microwave irradiation;
Stage #2: 1-methyl-piperazine With N-Bromosuccinimide In tetrahydrofuran; dimethyl sulfoxide at 0 - 23℃; for 0.5h; Inert atmosphere; chemoselective reaction;
50%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one
147676-70-8

5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one With 1,10-Phenanthroline; potassium pyrosulfite; tetraethylammonium bromide; sodium formate; palladium diacetate; triphenylphosphine In dimethyl sulfoxide at 70℃; for 3h; Inert atmosphere; Microwave irradiation;
Stage #2: 1-methyl-piperazine With N-Bromosuccinimide In tetrahydrofuran; dimethyl sulfoxide at 0 - 23℃; for 0.5h; Inert atmosphere; chemoselective reaction;
37%
ethyl 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzimidate
383427-84-7

ethyl 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)-benzimidate

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

A

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamine

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamine

B

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetateA 22.6%
B n/a
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one
139756-21-1

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With chlorosulfonic acid 1), 2) EtOH; Multistep reaction;
5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
960009-37-4

5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

ethanol
64-17-5

ethanol

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide at 110℃; under 1324.03 - 2942.29 Torr; for 6h;
With dicyclohexyl-carbodiimide at 105 - 110℃; under 1324.03 - 2942.29 Torr;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

Merrifield resin-OC(O)CH2CH2CH(OH)CH2I

Merrifield resin-OC(O)CH2CH2CH(OH)CH2I

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iPr2NEt / dimethylformamide
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
5-chlorosulfonyl-2-hydroxybenzoic acid
17243-13-9

5-chlorosulfonyl-2-hydroxybenzoic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iPr2NEt / dimethylformamide
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylformamide / 60 °C
1.2: polymer-supported HOBt; PyBrOP / dimethylformamide
1.3: isocyanate resin / tetrahydrofuran
2.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: Et3N, DMAP / CH2Cl2
2: NaOH / ethanol; H2O
3: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine / toluene / 70 - 75 °C
View Scheme
[N'-(1-cyano-butyl)-N-methyl-hydrazino]-acetic acid ethyl ester
304435-81-2

[N'-(1-cyano-butyl)-N-methyl-hydrazino]-acetic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 90 percent / MnO2
2.1: 90 percent / polymer-supported BEMP / ethanol
3.1: NH3
4.1: dimethylformamide / 60 °C
4.2: polymer-supported HOBt; PyBrOP / dimethylformamide
4.3: isocyanate resin / tetrahydrofuran
5.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
[N'-(1-cyano-butylidene)-N-methyl-hydrazino]-acetic acid ethyl ester

[N'-(1-cyano-butylidene)-N-methyl-hydrazino]-acetic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 90 percent / polymer-supported BEMP / ethanol
2.1: NH3
3.1: dimethylformamide / 60 °C
3.2: polymer-supported HOBt; PyBrOP / dimethylformamide
3.3: isocyanate resin / tetrahydrofuran
4.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester
304435-83-4

4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NH3
2.1: dimethylformamide / 60 °C
2.2: polymer-supported HOBt; PyBrOP / dimethylformamide
2.3: isocyanate resin / tetrahydrofuran
3.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
2-hydroxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid
960009-35-2

2-hydroxy-5-(4-methylpiperazin-1-ylsulphonyl)benzoic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dimethylformamide / 60 °C
1.2: polymer-supported HOBt; PyBrOP / dimethylformamide
1.3: isocyanate resin / tetrahydrofuran
2.1: 100 percent / NaOEt / ethanol / 0.17 h / 120 °C / microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine / toluene / 70 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane
2: sodium hydroxide / diethylene glycol
3: triethylamine
4: dicyclohexyl-carbodiimide / 105 - 110 °C / 1324.03 - 2942.29 Torr
View Scheme
2-ethoxybenzoyl chloride
42926-52-3

2-ethoxybenzoyl chloride

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N, DMAP / CH2Cl2
2: NaOH / ethanol; H2O
3: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 1.5 h / 20 °C
2: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
3: chlorosulfonic acid / 12 h / 20 - 30 °C
4: dichloromethane / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 2 h
2.1: chlorosulfonic acid; thionyl chloride / dichloromethane / 2 h
3.1: dichloromethane / 2 h
3.2: 4 h / Reflux
View Scheme
4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-03-9

4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / ethanol; H2O
2: 1) ClSO3H / 1), 2) EtOH
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
2: chlorosulfonic acid / 12 h / 20 - 30 °C
3: dichloromethane / 20 - 30 °C
View Scheme
2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)benzaldehyde
332374-42-2

2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)benzaldehyde

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; butanone; 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide3.3 g (53%)
4-Amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxylate

4-Amino-1-methyl-3-n-propyl-1H-pyrazole-5-carboxylate

2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamidine
383427-89-2

2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzamidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene; toluene
4-[2-Fluoro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-[2-Fluoro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In ethanol; hexane; dichloromethane; ethyl acetate
4-[2-Chloro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-[2-Chloro-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

viagra
139755-83-2

viagra

Conditions
ConditionsYield
In ethanol
Glauber's salt

Glauber's salt

ethyl 4-((4-ethoxy-3-[1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-onyl]phenyl)sulfonyl)piperazinecarboxylate
226956-41-8

ethyl 4-((4-ethoxy-3-[1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-onyl]phenyl)sulfonyl)piperazinecarboxylate

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With aq. sodium hydroxide; sodium chloride In tetrahydrofuran; dichloromethane
5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one
1033443-96-7

5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid
1093065-12-3

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane; water Suzuki Coupling; Inert atmosphere; Reflux;
5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine
1093065-15-6

5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine With hydrogenchloride; water In methanol at 75℃; for 4.5h;
Stage #2: With sodium hydroxide In methanol; water pH=14;
5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine
864164-45-4

5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
ConditionsYield
Stage #1: 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine With hydrogenchloride; water In methanol at 75℃; for 4h;
Stage #2: With sodium hydroxide In methanol; water pH=14;
ethyl bromide
74-96-4

ethyl bromide

5-[2-hydroxy-5-(4-methylpiperazine-1-ylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-[2-hydroxy-5-(4-methylpiperazine-1-ylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With triethylamine In toluene at 70 - 75℃;49 %Chromat.
viagra
139755-83-2

viagra

citric acid
77-92-9

citric acid

sildenafil citrate

sildenafil citrate

Conditions
ConditionsYield
In methanol; toluene for 1h; Product distribution / selectivity; Heating / reflux;99.7%
In ethanol for 1h; Product distribution / selectivity; Heating / reflux;96.2%
In acetone at 55℃; for 0.5h; Reflux;96.52%
viagra
139755-83-2

viagra

sildenafil hydrochloride
252920-86-8

sildenafil hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether for 4h;99%
With hydrogenchloride In propan-1-ol; acetone for 2h; Product distribution / selectivity; Heating / reflux;
With hydrogenchloride In propan-1-ol; toluene for 24h;
With hydrogenchloride In propan-1-ol for 1h; Product distribution / selectivity; Heating / reflux;
viagra
139755-83-2

viagra

1-[[3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-4-oxido-piperazine
1094598-75-0

1-[[3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-4-oxido-piperazine

Conditions
ConditionsYield
Stage #1: viagra With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at -10℃; for 2.5h;
Stage #2: With potassium carbonate In dichloromethane; water at 0℃; for 0.5h;
92%
viagra
139755-83-2

viagra

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid
1357931-55-5

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid; water at 20 - 100℃; for 41h;50%
Chloromethyl acetate
625-56-9

Chloromethyl acetate

viagra
139755-83-2

viagra

1-(acetoxymethyl)-4-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)-1-methylpiperazin-1-ium iodide
1402916-50-0

1-(acetoxymethyl)-4-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)-1-methylpiperazin-1-ium iodide

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 20℃;42%
acetonitrile
75-05-8

acetonitrile

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate acetonitrile solvate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate acetonitrile solvate

Conditions
ConditionsYield
With sulfuric acid In water for 1h; Heating / reflux;
ethanol
64-17-5

ethanol

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate hemiethanol solvate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hydrogensulphate hemiethanol solvate

Conditions
ConditionsYield
With sulfuric acid at 20℃; Heating / reflux;
viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemisulphate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemisulphate

Conditions
ConditionsYield
With sulfuric acid In toluene at 20 - 50℃; for 72.5h;
L-Tartaric acid
87-69-4

L-Tartaric acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemitartrate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine hemitartrate

Conditions
ConditionsYield
In ethanol at 20℃; for 13h; Heating / reflux;
ethanesulfonic acid
594-45-6

ethanesulfonic acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine esylate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine esylate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1 - 2h; Product distribution / selectivity; Heating / reflux;
In acetonitrile at 20℃; for 13h; Heating / reflux;
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

viagra
139755-83-2

viagra

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine fumarate

1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulphonyl]-4-methylpiperazine fumarate

Conditions
ConditionsYield
In ethanol; acetonitrile at 20℃; for 14h; Heating / reflux;

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