1,2-Dichloroethane → HCID 178522829, compound

Participants

Reaction Steps

To a solution of cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid (L) (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 (0.019 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 cis 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid benzylamide (Example 10) (12 mg): 1H NMR (300 MHz, CD3OD) δ 7.40-7.20 (m, 9 H), 4.39 (s, 2 H), 3.81 (m, 1 H), 2.45 (m, 1 H), 2.02-1.77 (m, 8 H); mass spectrum m/z 349 [(M+H)+; calcd for C21H25N4O: 349].

Provenance & Evidence