Sodium cyanoborohydride → 1-(1,3-Dimethyl-1H-pyrazol-4-yl)-N-((1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazol-5-yl)methyl)-N-methylmethanamine

Participants

Reaction Steps

A solution of 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazole-5-carbaldehyde (33) (39 mg, 0.10 mmol), 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamine (15 mg, 0.11 mmol), sodium cyanoborohydride (30 mg, 0.11 mmol) and DMF/acetic acid (10/1, 1 mL) was stirred at room temperature overnight. The reaction mixture was directly loaded on to reverse phase preparative HPLC column and purified to yield 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-((1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)sulfinyl)-1H-imidazol-5-yl)methyl)-N-methylmethanamine (501). 1H NMR (400 MHz, CDCl3) δ: 7.63 (s, 1H), 7.52 (s, 1H), 7.45-7.36 (m, 1H), 7.24-7.09 (m, 4H), 6.90-6.85 (m, 1H), 4.87 (d, J=13.0, 1H), 4.58 (d, J=13.0, 1H), 4.27 (d, J=14.5, 1H), 4.11 (s, 1H), 3.99 (d, J=13.2, 1H), 3.90-3.79 (m, 4H), 2.57 (s, 3H), 2.18 (s, 3H). LC-MS ESI m/z; found 506.2 [M+H]+.

Provenance & Evidence