Triethylamine → HCID 178425212, compound

Participants

Reaction Steps

A mixture of 3-chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)benzoic acid (80 mg, 0.23 mmol), 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (130 mg, 0.34 mmol) and triethylamine (70 mg, 0.69 mmol) in dichloromethane (20 mL) was stirred at room temperature for 2 hours. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (42 mmg, 0.28 mmol) was added. The resultant mixture was stirred at room temperature for additional 15 hours. To the reaction mixture, water (30 mL) was added. The mixture was extracted with dichloromethane (30 mL×3). The organic layers were combined and concentrated to give a residue in vacuo. The residue was purified by preparative-HPLC to give 3-Chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide I-8 as a white solid (80 mg, 72%). LRMS (M+H+) m/z: calcd 485.13. found 485. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, d6-DMSO): δ 11.49 (s, 1H), 9.39 (s, 1H), 9.04 (d, J=5.1 Hz, 1H), 8.57-8.56 (m, 1H), 8.17 (d, J=1.2 Hz, 1H), 8.05 (d, J=5.1 Hz, 1H), 7.93 (d, J=9 Hz, 1H), 7.83-7.73 (m, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 5.87 (s, 1H), 4.30 (d, J=4.8 Hz, 2H), 2.18 (s, 3H), 2.12 (s, 3H).

Provenance & Evidence