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139755-83-2

Basic Information
CAS No.: 139755-83-2
Name: Sildenafil
Article Data: 43
Cas Database
Molecular Structure:
Molecular Structure of 139755-83-2 (Sildenafil)
Formula: C22H30N6O4S
Molecular Weight: 474.584
Synonyms: 4-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,8,9-tetrazabicyclo[4.3.0]nona-3,7,10-trien-2-one;Piperazine,1-[[3-(4,7-dihydro-1-methyl-7- oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin- 5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-;Serum Albumin Iodine;Sildenafil Mesylate;Hongdenafil (Acetildenafil);
EINECS: 200-659-6
Density: 1.39 g/cm3
Melting Point: 187-189 ºC
Boiling Point: 672.4 ºC at 760 mmHg
Flash Point: 360.5 ºC
Solubility: Slightly soluble in water, methanol; very slightly soluble in ethanol, chloroform
Appearance: White crystalline powder
Hazard Symbols: Xi,T,F
Risk Codes: 36/37/38-39/23/24/25-23/24/25-11
Safety: 22-24/25-36-26-45-36/37-16-7
Transport Information: N/A
PSA: 121.80000
LogP: 2.56750
Synthetic route
200575-15-1

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

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
109-01-3

1-methyl-piperazine

139756-22-2

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

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%
139756-22-2

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

34352-59-5, 50398-09-9, 51545-09-6

1-methylpiperazine hydrochloride

Conditions
ConditionsYield
With triethylamine; N-ethyl-N,N-diisopropylamine In water at 60℃; for 1.2h;91.8%
1033861-39-0

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

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%
1033861-54-9

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

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%
109-01-3

1-methyl-piperazine

226956-42-9

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

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%
109-01-3

1-methyl-piperazine

1491216-01-3

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

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%
109-01-3

1-methyl-piperazine

147676-70-8

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

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%
383427-84-7

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

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

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

1-methyl-piperazine

139756-21-1

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

Conditions
ConditionsYield
With chlorosulfonic acid 1), 2) EtOH; Multistep reaction;
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History

 Sildenafil (CAS NO.139755-83-2) (compound UK-92,480) was synthesized by a group of pharmaceutical chemists working at Pfizer's Sandwich, Kent, research facility in England. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a symptom of ischaemic heart disease).

Specification

Sildenafil(CAS NO.139755-83-2), its Synonyms are 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine; Revatio; Viagra; Piperazine, 1-((3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methyl-. It is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It acts by inhibiting cGMP specific phosphodiesterase type 5, an enzyme that regulates blood flow in the penis.

Physical properties about Sildenafil are: (1)ACD/LogP: 2.468; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 2.45; (5)ACD/BCF (pH 5.5): 10.24 ; (6)ACD/BCF (pH 7.4): 42.36; (7)ACD/KOC (pH 5.5): 121.40; (8)ACD/KOC (pH 7.4): 502.20; (9)#H bond acceptors: 10; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.665; (13)Molar Refractivity: 126.026 cm3; (14)Molar Volume: 339.438 cm3; (15)Polarizability: 49.961 10-24cm3; (16)Surface Tension: 54.4710006713867 dyne/cm; (17)Density: 1.398 g/cm3; (18)Flash Point: 360.5 °C; (19)ES27:Take off immediately all contaminated clothing. nthalpy of Vaporization: 98.77 kJ/mol; (20)Boiling Point: 672.4 °C at 760 mmHg; (21)Vapour Pressure: 6.1E-18 mmHg at 25°C

When you are using Sildenafil, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable protective clothing;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/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) ;
(2)InChIKey=BNRNXUUZRGQAQC-UHFFFAOYSA-N; (3)Smilesc1(c2nc3c(c(=O)[nH]2)n(nc3CCC)C)c(ccc(c1)S(=O)(=O)N1CCN(CC1)C)OCC