2-Methylbenzimidazole → HCID 49785640, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-bromo-pyridin-4-yl)-[6-(4-dimethylamino-piperidin-1-yl)-1H-benzoimidazol-2-yl]-methanone (0.46 mmol, 1.0 mol eq.) [Example 102 (Method 1, Step 3)], 2-methyl benzimidazole (0.56 mmol, 1.2 mol eq), CuI (0.047 mmol, 0.5 mol eq.), (1R,2R)—N,N′-dimethyl-cyclohexane-1,2-diamine (0.093 mmol, 0.2 mol eq.) in 2 mL of DMF was heated at 130° C. for 48 h under nitrogen. The reaction was diluted with 50 mL EtOAc and 50 mL brine. The organic layer was separated and dried over Na2SO4, filtered and evaporated to dryness. HPLC purification gave the title compound (31 mg, 14%). HRMS m/z 480.2502 (M+H)+. 1H NMR (400 MHz, DMSO-d6): 8.96 (1H, d), 8.65 (1H, s), 8.30 (1H, d), 7.74-7.63 (3H, m), 7.31-7.29 (2H, m), 7.17 (1H, d), 6.93 (1H, s), 4.16 (1H, bs), 3.77-3.74 (2H, m), 2.80-2.71 (2H, m), 2.70 (3H, s), 2.20 (6H, s), 1.89-1.85 (2H, m), 1.57-1.48 (2H, m).

Provenance & Evidence