HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylpiperazine → Desmethyl Carbodenafil
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzoic acid | HCID 135565085 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Desmethyl Carbodenafil | HCID 135430839 | 25.3% |
Reaction Steps
A solution of 4-ethoxy-3-(1-methyl-7-oxo-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-5-yl)benzoic acid (0.095 g, 0.00027 mol), 1-methylpiperazine (0.265 g, 0.00265 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.077 g, 0.0004 mol) and 1-hydroxybenzotriazole (0.054 g, 0.0004 mol) in dichloromethane (25 ml) was stirred at room temperature for 18 hours. The reaction solution was washed with water (25 ml), dried (MgSO4) and evaporated under vacuum, and then the resulting residue crystallised from ethyl acetate-hexane to give the title compound as colourless crystals (0.03 g, 25%), m.p. 196°-197° C. Found: C,63.12; H,6.81; H,18.96. C23H30N6O3 requires C,62.99; H,6.90; N,19.16%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05426107 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-50043380321c47b6b797d115d52b2832 |
| Source note | uspto-grants-1995_06 |