Ammonia → HCID 178519830, compound

Participants

Reaction Steps

To a stirred solution of 0.044 g of trans-1,3-dihydro-1-{4-(1-piperazinyl)-1-cyclohexyl}-2H-benzimidazol-2-one and 20 mL of triethylamine in 3 mL of dichloromethane was added 0.03 g of pyrimidine-5-carboxylic acid chloride. After 2 h, 5 mL of dilute aqueous ammonia was added and the mixture stirred for an additional 30 min. The organic layer was separated, the aqueous layer extracted with two additional 20 mL portions of chloroform and the combined organic extracts dried over MgSO4 and concentrated under reduced pressure. Chromatography over silica gel eluting with 90:10 EtOAc: MeOH gave 0.030 g of trans-1,3-dihydro-1-{4-[4-(5-pyrimidinecarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: mp>250° C.; 1H NMR (400 MHz, CDCl3) 9.76 (bs 1H), 9.27 (s, 1H), 8.83 (s, 2H), 7.27-7.04 (m, 4H), 4.27 (br t, 1H), 3.84 (br s, 2H), 3.43 (br s, 2H), 2.73 (br s, 1H), 2.61 (br s, 2H), 2.54 (d, 1H), 2.34 (q, 2H), 2.02 (br t, 3H), 1.97 (br s, 1H), 1.52 (q, 2H). The dihydrochloride salt was recystallized from ethanol: Analysis calculated for C22H26N6 O2.2HCl.0.65 CHCl3C: 48.84, H: 5.18, N: 15.09; found C: 48.85, H: 5.36, N: 14.72.

Provenance & Evidence