1,2-Dichloroethane → HCID 178522830, compound

Participants

Reaction Steps

To a solution of trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid (M) (20 mg, 0.07 mmol) in DMF (0.2 mL) was added EDC (26 mg, 0.14 mmol), HOBt (18 mg, 0.14 mmol), triethylamine (0.007 mL, 0.14 mmol) and benzyl amine (0.007 mL, 0.7 mmol). The reaction mixture was stirred at room temperature for 1 h followed by quenching with aqueous NaHCO3 and EtOAc. The layers were separated and the organic was washed twice with water, dried over Na2SO4, filtered and concentrated. Purification of the crude oil by preparative reverse-phase HPLC gave trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid benzylamide (Example 9) (14 mg): 1H NMR (300 MHz, CD3OD) δ 7.40-7.20 (m, 9H), 4.39 (s, 2H), 3.55 (m, 1H), 2.31 (m, 1H), 2.20 (br d, 2H), 1.98 (br d, 2H), 1.77 (m, 2H), 1.50 (m, 2H); mass spectrum m/z 349 [(M+H)+; calcd for C21H25N4O: 349].

Provenance & Evidence