Phenethylamine → HCID 71117993, compound

Participants

Reaction Steps

A solution of 2-((2-chloro-6-fluorobenzyl)thio)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylic acid (88) (50 mg, 0.13 mmol), N-benzylmethylamine (16 mg, 0.13 mmol), triethylamine (0.12 mL, 0.79 mmol) and propylphosphonic anhydride (T-3-P)(50% in ethyl acetate, 0.12 mL, 0.20 mmol) in dichloromethane (1.5 mL) was stirred overnight at room temperature. The reaction was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (50%-100% EtOAc in hexanes) to give N-benzyl-2-((2-chloro-6-fluorobenzyl)thio)-1-(4-fluorophenyl)-N-methyl-1H-imidazole-5-carboxamide (500). 1H NMR (400 MHz, CDCl3) δ: 7.37-7.25 (m, 4H), 7.20-6.99 (m, 8H), 6.93-6.90 (m, 1H), 4.64 (s, 2H), 4.45 (s, 2H), 2.96 (s, 3H). LC-MS ESI m/z; found 484.1 [M+H]+.

Provenance & Evidence