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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206185Generated: November 1, 2026

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-N-methylbenzamide

https://huagongshe.com/reaction/2206185

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant1-Hydroxybenzotriazole hydrateHCID 2796029—
ReactantMethylamine hydrochlorideHCID 6364545—
Reactant4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoic acidHCID 117988440—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventTriethylamineHCID 8471—
Product4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-N-methylbenzamideHCID 117987531100.1%

Reaction Steps

To a solution of 4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoic acid (2.59 g), methylamine hydrochloride (688 mg), HOBt monohydrate (1.56 g) and triethylamine (1.89 mL) in DMF (20 mL) was added EDCI hydrochloride (1.95 g) at 0° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the white precipitate was filtered, washed with water and hexane, and dried in vacuum to give the title compound (2.68 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09371320B2
Source datasetuspto-grants-2016_06
ORD IDord-2631d1a734c649989798b89f4deae404
Source noteuspto-grants-2016_06