Dimethylamine → 3-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]phenyl}-N,N-dimethylpropanamide

Participants

Reaction Steps

TBTU (188 mg; 0.58 mmol; 1.3 eq.) was added to a cooled (0° C.) solution of 3-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]phenyl}propanoic acid (150 mg; 0.45 mmol; 1.0 eq.) and DIEA (176 μl; 1.03 mmol; 2.3 eq.) in DMF (3 mL). After 10 min, dimethylamine (270 μl of a 2.00 M in THF; 0.54 mmol; 1.20 eq.) was added and the reaction mixture was stirred overnight at RT. The resulting solid was filtered off and purified by preparative HPLC to afford the title compound as a brown solid. 1H NMR (300 Mz, DMSO-d6) δ: 13.34 (brs, 1H), 9.26 (s, 1H), 8.36 (d, J=8.1 Hz, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.62-7.59 (m, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.46-7.41 (m, 1H), 7.28-7.23 (m, 1H), 2.96 (s, 3H), 2.93-2.88 (m, 2H), 2.83 (s, 3H), 2.70-2.65 (m, 2H). HPLC (Condition A): Rt 3.23 min (purity 92.2%). MS (ESI+): 361.3, MS (ESI−): 359.3.

Provenance & Evidence