Tert-Butyl nitrite → HCID 178510242, compound

Participants

Reaction Steps

To a solution of N-({3-[(2-amino-3-chloro-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (38 mg, 0.080 mmol) in Acetonitrile (10 ml) was added tert-butyl nitrite (0.021 ml, 0.161 mmol) and the reaction mixture was stirred at RT for 2 hours. The reaction was quenched with methanol, the solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyano-4-fluorophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (17 mg, 0.037 mmol, 46% yield). 1H NMR (DMSO-d6) δ ppm 8.25 (br. s., 1H) 7.74 (s, 1H) 7.69 (dd, 1H) 7.60 (t, 1H) 7.45 (d, 1H) 7.32 (t, 1H) 4.48 (d, 2H). LC-MS (ES+) m/z 457.05, [M+H].

Provenance & Evidence