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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1409413Generated: October 30, 2026

Dimethylformamide → N-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((R)-2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxamide

https://huagongshe.com/reaction/1409413

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 67170882—
ReactantHCID 86714632HCID 86714632—
SolventDichloromethaneHCID 6344—
ProductN-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((R)-2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxamideHCID 8671465576.8%

Reaction Steps

The title compound was prepared using the procedure described in Example 3(h) starting from (R)-1-(2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxylic acid (1.059 mmol, 195 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-benzonitrile (0.882 mmol, 230 mg) using DMF (2 ml) as the solvent. DCM was added and evaporated. The residue was purified by flash chromatography. The product was further purified by dissolving it in MeOH/DCM and washing twice with 1 M NaHCO3. The separated organic phase was dried, purified and evaporated. 289 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.02-1.10 (m, 6H), 2.34 (s, 3H), 3.70-3.91 (m, 3H), 4.22-4.48 (m, 3H), 4.92 (d, 1H), 6.95 (d, 1H), 7.47 (s, 1H), 7.83 (d, 1H), 7.97-8.00 (m, 2H), 8.04 (d, 1H), 8.09-8.13 (m, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921378B2
Source datasetuspto-grants-2014_12
ORD IDord-a3aab1a89ad44179886b788971f21420
Source noteuspto-grants-2014_12