Thiazole-4-carboxaldehyde → HCID 67496202, compound

Participants

Reaction Steps

To a solution of (S)-3-(2-amino-3-phenylpropanamido)-5-(pyridin-4-yl)benzoic acid (45.1) (181 mg, 0.50 mmol) in DCM (5 mL) was added thiazole-4-carbaldehyde (56 mg, 0.50 mmol). The mixture was stirred for 1 h, sodium triacetoxyborohydride (212 mg, 1.00 mmol) was then added and the mixture stirred for an additional 1 hour at room temperature. The reaction mixture was then concentrated and the crude product purified by reverse phase chromatography (0-100% CH3CN/water+0.5% TFA) to afford (S)-3-(3-phenyl-2-(thiazol-5-ylmethylamino)propanamido)-5-(pyridin-4-yl)benzoic acid (45.2) as a white solid (82 mg, 36% yield). LCMS ESI (pos.) m/e: 459.0 (M+1). 1H NMR (500 MHz, MeOH-D4) δ ppm 9.13 (d, J=1.96 Hz, 1H), 8.93 (d, J=6.85 Hz, 2H), 8.35 (d, J=1.22 Hz, 1H), 8.32-8.34 (m, 2H), 8.31 (t, J=1.83 Hz, 1H), 8.18-8.23 (m, 1H), 7.82 (d, J=1.96 Hz, 1H), 7.23-7.37 (m, 5H), 4.48-4.58 (m, 2H), 4.35 (dd, J=9.29, 5.87 Hz, 1H), 3.41-3.51 (m, 1H), 3.24-3.30 (m, 1H).

Provenance & Evidence