Tetrahydrofuran → 1H-Benzoimidazole-2-carboxylic acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide

Participants

Reaction Steps

The reaction was carried out as described in General Procedure 2 using 2-trichloromethyl-1H-benzoimidazole (Example 1, 100 mg, 0.42 mmol) and 8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine dihydrochloride (172 mg, 0.84 mmol) in tetrahydrofuran (THF, 3 mL). Purification afforded 10 mg (10%) of the title compound. MS (ESI): mass calculated for C16H20N4O, 284.16; m/z found, 285.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.70 (br s, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.76 (br s, 1H), 7.43 (br s, 1H), 7.35-7.33 (m, 2H), 4.37 (q, J=7.1 Hz, 1H), 3.25-3.23 (m, 2H), 2.49 (s, 3H), 2.39-2.33 (m, 2H), 2.23 (s, 3H), 2.23-2.18 (m, 2H), 2.02-1.96 (m, 2H), 1.97 (d, J=14.4 Hz, 2H).

Provenance & Evidence