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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 660937Generated: October 30, 2026

Acetic Acid → Rac-2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

https://huagongshe.com/reaction/660937

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantDimethylformamideHCID 6228—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 2782448—
SolventWaterHCID 962—
ProductRac-2-[4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamideHCID 58011689—

Reaction Steps

50.0 mg (0.171 mmol) of 4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 130A, 35.5 mg (0.188 mmol) of 1-[3-(trifluoromethyl)phenyl]-ethylamine and 27.7 mg (0.205 mmol) of HOBt are placed in 1.5 ml of dimethylformamide and treated with 42.6 mg (0.222 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then stirred with 19 ml of water and the resulting precipitate recovered by filtration. The crude product is washed with water, dried in vacuo and purified by preparative HPLC [Method 9]. 14 mg (18% of theory) of the target compound are thus obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08084481B2
Source datasetuspto-grants-2011_12
ORD IDord-0d08feff096c4ef2af8624bc1af7db70
Source noteuspto-grants-2011_12