5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
Sildenafil
CAS: 139755-83-2
Molecular Formula: C22H30N6O4S
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Names and Identifiers
| Name | Sildenafil |
| Synonyms | Sildenafil Sildenafil Citrate 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazol[4,3d]pyrimidin-7-one |
| CAS | 139755-83-2 |
| 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) |
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Physico-chemical Properties
| Molecular Formula | C22H30N6O4S |
| Molar Mass | 474.576 |
| Density | 1.39g/cm3 |
| Boling Point | 672.4°C at 760 mmHg |
| Flash Point | 360.5°C |
| Vapor Presure | 6.1E-18mmHg at 25°C |
| Refractive Index | 1.664 |
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Nature
Open Data Verified Data
crystallized from methanol-dimethylformamide, melting point 187-189 °c.
Last Update：2024-01-02 23:10:35
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Preparation Method
Open Data Verified Data
3-n-propylpyrazole-5-carboxylic acid ethyl ester and dimethyl sulfate were mixed and reacted to obtain 1-methyl -3-n-propylpyrazole-5-carboxylic acid ethyl ester. This was suspended in sodium hydroxide solution and hydrolyzed to give 1-methyl -3-n-propyl pyrazole-5-carboxylic acid. The hydrolysate was added to the mixed acid in portions and nitrated to give 1-methyl-4-nitro-3-n-propylpyrazole-5-carboxylic acid. The nitrated product was chlorinated with thionyl chloride to acyl chloride, and then ammoniated with concentrated aqueous ammonia to give 1-methyl-4-nitro-3-n-propylpyrazole-5-carboxamide. The carboxamide and tin dichloride dihydrate were suspended in ethanol and reduced by reflux to give 4-amino -1-methyl -3-n-propyl pyrazole-5-carboxamide. The reduced product, 4-= methylaminopyridine and triethylamine were dissolved in dichloromethane, and then 2-ethoxybenzoyl chloride in dichloromethane was added to obtain 4-(2-ethoxybenzoylamino).-1-methyl-3-n-propylpyrazole-5-carboxamide. The acylation product in sodium hydroxide aqueous solution and hydrogen peroxide under the action of ring synthesis of 5-(2-ethoxyphenyl)-1-methyl -3-n-propyl -1, 6-= hydro-7h-pyrazolo [4,3-d] pyridin-7-one. The cyclization product was added portionwise to chlorosulfonic acid to give 5-(5-chlorosulfonic 2-ethoxyphenyl)-1-methyl -3-n-propyl 1,6-= hydrogen -7H-pyrazolo [4,3-d] pyridin-7-one. The chlorosulfonated product was suspended in ethanol, 4 methyl piperazine was added, and Sildenafil was obtained by stirring.
Last Update：2022-01-01 09:24:27
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Quality Standard
Open Data Verified Data
sildenafil limonic acid: content should be greater than or equal to 99%; Loss on drying should be less than 0.5%; Burning residue should be less than 0.5%; Heavy metal content should be less than 0. 002%.
Last Update：2022-01-01 09:24:28
5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one - Use
Open Data Verified Data
manufactured by Pfizer Group, USA, was first launched in the United States in 1998. It is a selective inhibitor of phosphodiesterase (PDE)V and can enhance the physiological response to penile erection caused by NO release under sexual stimulation. Mainly used for erectile dysfunction.
Last Update：2022-01-01 09:24:28
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