Isopropylamine → HCID 70145076, compound

Participants

Reaction Conditions

Reaction Steps

Isopropylamine (227.8 mg, 3.85 mmol) was added to (±)-(1S*,2R*,4R*)-4-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)cyclohexane-1,2-diol (Example 51, part b, 146.5 mg, 385.4 mmol) in ethanol (3.9 ml) and the reaction was heated at 100° C. in a sealed tube for 68 hr. The reaction was cooled, saturated sodium carbonate added, extracted with ethyl acetate, dried with magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with methanol:ethyl acetate (1:19) to give the title compound (104.1 mg, 75%). Rf=0.20 (1:19 methanol:ethyl acetate); 1H-NMR (CD3OD, 300 MHz) δ7.53 (s, 1H), 7.36 (s, 1H), 4.31 (tt, 1H, J=13, 4), 4.06 (h, 1H, J=7), 3.97 (s, 1H), 3.75-3.68 (m, 1H), 2.50 (q, 1H, J=12), 2.39 (dq, 1H, J=13, 4), 2.02-1.96 (m, 1H), 1.78-1.49 (m, 3H), 1.29 (d, 3H, J=7), 1.28 (d, 3H, J=7); MS (ES) M+H=358.

Provenance & Evidence