Diisopropylethylamine → HCID 178461793, compound

Participants

Reaction Steps

A solution of 2-thiazol-4-yl-3H-benzoimidazol-5-ylamine (1-6, 103 mg, 0.476 mmol), (2S)-2-Hydroxy-2-phenyl-propionic acid (79 mg, 0.48 mmol) and diisopropylethylamine (0.166 mL, 0.95 mmol) in N,N-dimethylformamide (5 mL) was reacted at the ambient temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBop, 273 mg, 0.52 mmol). After 3 h stirring at the same temperature, the reaction mixture was concentrated under the reduced pressure and the residue was partitioned between ethyl acetate (50 mL) and aqueous sodium bicarbonate solution (40 mL). The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. The resulting crude product was triturated with ethyl acetate (3 mL), collected by filtration, and dried under the reduced pressure to afford (2S)-2-Hydroxy-2-phenyl-N-[2-(1,3-thiazol-4-yl)-1H-benzimidazol-5-yl]propanamide as a white solid (3-62); 1H NMR (500 MHz, DMSO-d6) δ 12.88 (s, 1H), 9.72 (s, 1H), 9.31 (s, 1H), 8.42 (s, 1H), 8.12 (s, 1H), 7.65 (d, 2H, J=8.5 Hz), 7.52 (m, 1H), 7.36 (m, 3H), 7.26 (m, 1H), 6.45 (s, 1H), 1.72 (s, 3H).

Provenance & Evidence