Triethylamine → n-((1r)-1-{5-[5-Chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-4,4-difluorocyclohex-1-ene-1-carboxamide

Participants

Reaction Steps

The above carboxylic acid (223 mg, 1.37 mmol) and the compound of Reference Example 4 (482 mg, 1.37 mmol) were dissolved in 2.3 mL of degassed DMF. HOBT (21 mg, 0.14 mmol) and EDCI (303 mg, 1.58 mmol) were added, and the mixture was made basic with triethylamine (139 mg. 1.37 mmol). After 20 hours at ambient temperature, 10 mL of water and 1 mL of 10% sodium bicarbonate were added and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, and then dried over sodium sulfate. Filtration and removal of solvent provided the crude product which was subjected to chromatography on silica gel eluting with 5 to 50% EtOAc in hexanes to give N-((1R)-1-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-4,4-difluorocyclohex-1-ene-1-carboxamide

Provenance & Evidence