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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1532099Generated: November 1, 2026

1-Methylpiperazine → Desmethyl Carbodenafil

https://huagongshe.com/reaction/1532099

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 crystallized 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; N,18.96. C23H30N6O3 requires C,62.99; H,6.90; N,19.16%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06200980B1
Source datasetuspto-grants-2001_03
ORD IDord-f2a36881181349d9a991134aa33e1e4f
Source noteuspto-grants-2001_03