Acetic Acid → HCID 24831471, compound

Participants

Reaction Steps

To a solution of 5-[5,6-bis(methyloxy)-1H-benzimidazol-1-yl]-3-[((1R)-1-{2-chloro-3-[(4-piperidinylmethyl)amino]phenyl}ethyl)oxy]-2-thiophenecarboxamide (Example 40, 86 mg, 0.015 mmol) in 2 mL of DCM and 1 mL of MeOH was added formaldehyde (23 μl, 0.30 mmol) and acetic acid (10 μl, 0.18 mmol). After 10 min, sodium triacetoxyborohydride (49 mg, 0.23 mmol) was added and the reaction was stirred for 16 h. The solution was diluted with DCM and washed with saturated NaHCO3 solution and water, dried over MgSO4 and concentrated to give 49 mg of the title compound (56%). 1H NMR (400 MHz, d6-DMSO) δ 8.31 (s, 1H), 7.78 (br s, 1H), 7.28 (s, 1H), 7.13 (t, J=7.8 Hz, 1H), 7.07 (br s, 1H), 7.01-7.00 (m, 2H), 6.76 (d, J=7.6 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 5.92 (m, 1H), 5.39 (m, 1H), 3.77 (s, 3H), 3.74 (s, 3H), 2.95 (m, 2H), 2.65 (m, 2H), 2.06 (s, 3H), 1.70-1.56 (m, 7H), 1.12-1.09 (m, 2H). HRMS calculated C29H34ClN5O4S [M+H]+ 584.2098, found 584.2093.

Provenance & Evidence