Triethylamine → HCID 86759635, compound

Participants

Reaction Steps

4-Cyanobenzoyl chloride (0.30 g) was added to a stirred solution of the (R)-[2-(S)-methyl-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (Example 27; 0.40 g) and triethylamine (0.30 ml) in DCM (10 ml). The reaction mixture was allowed to stir at room temperature for 17 hours (overnight), and then partitioned between DCM (20 ml) and 2 M HCl (20 ml). The organic phase was separated, dried and concentrated to give a gum. The residue was purified by chromatography on an 8 g silica Biotage cartridge eluting 1:1 EtOAc/isohexane to give the title compound (0.445 g) as a white solid. NMR (DMSO-d6, 100° C.): 1.17 (d, 3H), 1.58 (s, 3H), 3.05-3.14 (m, 1H), 3.23-3.29 (m, 2H); 3.73 (brs, 1H), 3.88 (brs, 1H), 4.47 (d, 1H), 4.79 (brs, 1H), 6.79 (s, 1H), 7.58 (d, 2H), 7.88 (d, 2H); m/z 368.

Provenance & Evidence