Trifluoroacetic acid → HCID 49833859, compound

Participants

Reaction Steps

1,1-dimethylethyl 6-[4-(chlorocarbonyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-1H-benzimidazole-1-carboxylate (33 mg, 0.08 mmol), was taken into dichloromethane (1.5 mL) followed by addition of homopiperidine (0.1 mL, 0.89 mmol) and the mixture was allowed to stir for 12 h at room temperature. The mixture was then concentrated and the residue partitioned with ethyl acetate and 10% aqueous citric acid. The organic phase was separated and dried over magnesium sulfate then filtered and concentrated. The residue obtained was taken into trifluoroacetic acid (1 mL) and allowed to stand for 1 h at room temperature. The solution was then concentrated and the residue taken into a minimum of aqueous acetonitrile and purified by preparative reverse phase HPLC. Lyophilization of the combined pure fractions afforded 4-(azepan-1-ylcarbonyl)-7-(2-methyl-1H-benzimidazol-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (18 mg) as an amorphous solid. 1H NMR (400 MHz, d6-DMSO): 7.91 (s, 1H), 7.83 (d, 1H), 7.76 (dd, 1H), 7.64 (d, 1H), 7.55 (dd, 1H), 7.06 (d, 1H), 4.42 (s, 2H), 4.22 (br s, 2H), 3.55 (br s, 2H), 3.29 (tr, 4H), 2.64 (s, 3H), 1.65 (br s, 4H), 1.49 (br s, 4H). MS (EI) for C24H28N4O2: 406 (MH+).

Provenance & Evidence