Acetic Acid → HCID 67497262, compound

Participants

Reaction Steps

To a solution of a 1:9 mixture of (2S)-2-amino-N-(2-methoxy-5-(1H-pyrazol-4-yl)pyridin-3-yl)-3-phenylpropanamide 15.1.D and (S)-2-amino-N-(2-oxo-5-(1H-pyrazol-4-yl)-1,2-dihydropyridin-3-yl)-3-phenylpropanamide (90 mg, 0.28 mmol) in DCM (1 mL) was added thiazole-4-carbaldehyde (26 mg, 0.28 mmol) and was then stirred for 1 hour. Sodium triacetoxyborohydride (170 mg, 0.82 mmol) and acetic acid (16 μL, 0.28 mmol) was then added, the mixture was stirred for an additional 1 hour at room temperature, concentrated and the crude product purified by reverse phase chromatography (0-100% CH3CN/water+0.5% TFA) to afford (2S)—N-(2-methoxy-5-(1H-pyrazol-4-yl)pyridin-3-yl)-3-phenyl-2-(thiazol-5-ylmethylamino)propanamide 15.1 (5.7 mg, 57%) as a white solid. LCMS ESI (pos.) m/e: 435.1 (M+1): 1H NMR (500 MHz, MeOH-D4) δ ppm 9.13 (d, J=1.83 Hz, 1H), 8.50 (d, J=1.83 Hz, 1H), 8.15 (d, J=1.83 Hz, 1H), 7.94 (s, 2H), 7.80 (d, J=1.83 Hz, 1H), 7.25-7.39 (m, 5H), 4.46-4.56 (m, 3H), 3.91 (s, 3H), 3.41 (dd, J=13.43, 6.10 Hz, 1H), 3.24 (dd, J=13.43, 9.16 Hz, 1H).

Provenance & Evidence