Isobutyraldehyde → HCID 57774411, compound

Participants

Reaction Steps

To a solution of (5S)-3-(3,3-dimethylbutyl)-5-(2-oxo-2-(4-(2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3(2H)-yl)piperidin-1-yl)ethyl)-2-(2-(piperidin-4-yl)thiazol-5-yl)thiazolidin-4-one (30 mg, 0.04 mmol, 1 eq) in DCM (3 mL) was added isobutyraldehyde (6 mg; 0.08 mmol, 2 eq) and NaBH(OAc)3 (27 mg, 0.12 mmol, 3 eq). The reaction mixture was stirred at RT for 18 h, then quenched with MeOH (0.1 mL) and sat. NaHCO3 (1 mL). The reaction mixture was diluted with DCM (10 mL) and washed with water (5 mL), brine (5 mL), dried (MgSO4) and then concentrated in vacuo. The residue was purified by column chromatography over silica gel eluted with 2 to 10% MeOH in DCM to afford (5S)-3-(3,3-dimethylbutyl)-2-(2-(1-isobutylpiperidin-4-yl)thiazol-5-yl)-5-(2-oxo-2-(4-(2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3(2H)-yl)piperidin-1-yl)ethyl)thiazolidin-4-one (23 mg, 79% yield). (M+1) 695. 1H NMR (CDCl3) δ 7.70 (m, 3H), 6.90 (t, J=7.2 Hz, 1H), 6.70 (d, J=7.5 Hz, 1H), 6.49 (NH, 1H), 5.65 (m, 1H), 4.74 (m, 1H), 4.44 (m, 1H), 3.93 (m, 1H), 3.65 (m, 1H), 3.45-3.35 (m, 3H), 3.17-2.59 (m, 9H), 2.09-1.41 (m, 15H), 1.35 (m, 1H), 1.00-0.85 (m, 15H) ppm.

Provenance & Evidence