Triethylamine → HCID 86663704, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-6-(3-aminopiperidin-1-yl)-4-(4-(morpholine-4-carbonyl)phenylamino)-2-propoxynicotinamide (50 mg, 0.104 mmol), phenyl 5-methylthiazol-2-ylcarbamate (29.1 mg, 0.124 mmol), and Et3N (0.014 mL, 0.104 mmol) in THF (3 mL) in a scintillation vial was stirred at 60° C. for 2 hrs, during which time a white precipitate forms. Left standing overnight at rt. The solid were dissolved in a mixture of CH2Cl2 and MeOH and crude mixture was chromatographed (loaded onto an ISCO Companion 40 g silica gel column and eluted with (90:9:1 CH2Cl2:MeOH: NH4OH)/CH2Cl2 gradient (20-100%) to give 40 mg (R)-6-(3-(3-(5-methylthiazol-2-yl)ureido)piperidin-1-yl)-4-(4-(morpholine-4-carbonyl)phenylamino)-2-propoxynicotinamide as a white solid. LCMS: (M+H)+=623.37. 1H NMR (400 MHz, CDCl3) δ ppm 11.51 (1H, s), 7.93 (1H, br. s.), 7.38 (2H, d, J=8.57 Hz), 7.24 (2H, d, J=8.57 Hz), 6.80 (1H, s), 6.03 (1H, s), 5.94 (1H, br. s.), 4.23-4.37 (2H, m), 3.85-4.05 (2H, m), 3.55-3.82 (8H, m), 3.25-3.53 (4H, m), 2.32 (3H, s), 1.65-1.90 (5 H, m), 0.97 (3H, t, J=7.47 Hz).

Provenance & Evidence