3-Chloro-5-fluorobenzonitrile → HCID 58560983, compound

Participants

Reaction Steps

Sodium tert-butoxide (92 mg, 0.96 mmol) was added to a solution of 3-chloro-5-fluorobenzonitrile (67.9 mg, 0.359 mmol) and N-(4-{(1R)-1-[(R)-(4-chlorophenyl)(hydroxy)methyl]-4,4,4-trifluorobutyl}benzoyl)-β-alanine (prepared using the procedures from INTERMEDIATE 1 and the saponification step of EXAMPLE 1, 100 mg, 0.239 mmol) in DMF (3 mL), then the resulting brown mixture was stirred at 80° C. for 16 hours. The mixture was diluted with EtOAc, then washed with 2 N HCl(aq), then washed twice with water. The organic layer was then concentrated, and the resulting yellow residue was purified by reverse phase HPLC eluting with 30-100% MeCN/water+0.1% TFA. Following lyophilization, this afforded the title compound. LC3 3.35 min. (M+H)+ 577.

Provenance & Evidence