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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 21934Generated: October 30, 2026

1-Methylpiperazine → Desmethyl Carbodenafil

https://huagongshe.com/reaction/21934

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylpiperazineHCID 53167—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzoic acidHCID 135565085—
SolventDichloromethaneHCID 6344—
ProductDesmethyl CarbodenafilHCID 13543083925.3%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05426107
Source datasetuspto-grants-1995_06
ORD IDord-50043380321c47b6b797d115d52b2832
Source noteuspto-grants-1995_06