Thiazole-4-carboxaldehyde → HCID 178522001, compound

Participants

Reaction Steps

To a solution of (2S)—N-(3-(1H-pyrazol-3-yl)phenyl)-2-amino-3-phenylpropanamide 12.C (200 mg, 0.65 mmol) in DCM (5 mL) was added thiazole-4-carbaldehyde (73 mg, 0.65 mmol, available from Combi-Blocks). The mixture was stirred for 1 h, then sodium triacetoxyborohydride (207 mg, 0.98 mmol) was added and the mixture stirred for an additional hour at room temperature. The mixture was then concentrated and the crude product purified by reverse phase chromatography (0-100% CH3CN/water+0.5% TFA) to afford (2S)—N-(3-(1H-pyrazol-3-yl)phenyl)-3-phenyl-2-(thiazol-4-ylmethylamino)propanamide 12 as a white solid (66.7 mg, 25% yield). LCMS ESI (pos.) m/e: 404.0 (M+1): 1H NMR (500 MHz, MeOH-D4) δ ppm 9.11 (d, J=1.96 Hz, 1H), 7.82-7.87 (m, 1H), 7.80 (d, J=1.96 Hz, 1H), 7.74 (d, J=2.20 Hz, 1H), 7.51-7.60 (m, 1H), 7.21-7.38 (m, 7H), 6.68 (d, J=2.20 Hz, 1H), 4.50 (d, J=5.38 Hz, 2H), 4.29 (dd, J=9.29, 5.87 Hz, 1H), 3.43 (dd, J=13.45, 5.62 Hz, 1H), 3.27 (dd, J=13.45, 9.29 Hz, 1H).

Provenance & Evidence