Sodium borohydride → HCID 178489057, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-methyl 4-(5-cyano-1H-benzo[d]imidazol-2-yl)-4-(5-methoxy-7-methyl-1H-indol-4-yl)-2-methylbutanoate (Example 151-B) (95 mg, 0.228 mmol) in MeOH (3 mL) was treated with sodium borohydride (220 mg, 6.7 mmol) and heated at 60° C. for 4 hours. The reaction was cooled to room temperature and quenched with a saturated solution of ammonium chloride. The product was extracted with ethyl acetate, the organics were dried over sodium sulfate, concentrated and purified via reversed phase FCC(C18 gold column, 10-70% ACN:water) to obtain the title compound as a mixture of diastereomes. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.89 (br. s., 1H) 7.96 (br. s., 1H) 7.55 (br. s., 1H) 7.46-7.52 (m, 1H) 7.15 (t, J=2.75 Hz, 1H) 6.79 (s, 1H) 6.14 (d, J=1.96 Hz, 1H) 5.01 (dd, J=10.39, 4.89 Hz, 1H) 3.70-3.81 (m, 3H) 3.17-3.23 (m, 1H) 3.09-3.16 (m, 1H) 2.45 (d, J=0.61 Hz, 3H) 2.38 (ddd, J=13.57, 10.39, 3.67 Hz, 1H) 2.14-2.24 (m, 1H) 1.21-1.33 (m, 2H) 0.95 (d, J=6.60 Hz, 3H). HRMS calcd. for C23H24N4O2 (M+H)+ 389.1975. found 389.1978.

Provenance & Evidence