HCID 86711711, compound → 1-[1-(8-acetyl-9-methyl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

N-Methoxy-N,9-dimethyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxamide (30 mg, 0.07 mmol) was dissolved into THF (2 mL) under nitrogen and cooled to −78° C. Methylmagnesium chloride (3 M in THF; 0.046 mL, 0.14 mmol) was added to the reaction mixture. The reaction was stirred at −78° C. for 30 minutes and slowly warmed to room temperature. After 1 hour, the crude reaction mixture was concentrated, diluted with ethyl acetate, washed with water and saturated potassium carbonate. The organic layer was collected, was concentrated, was dissolved into methanol and was purified by preparative HPLC to afford 1-[1-(8-acetyl-9-methyl-9H-purin-6-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (9.3 mg, 0.023 mmol, 34% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 8.35 (s, 1H), 7.20-7.14 (m, 1H), 6.96-6.88 (m, 3H), 6.27-4.92 (m, 2H), 4.66-4.45 (m, 1H), 3.93 (s, 3H), 3.42-3.20 (m, 2H), 2.63 (s, 3H), 2.42-2.26 (m, 2H), 1.87 (br d, 2H). MS (EI) for C20H21N7O2: 392 (MH+).

Provenance & Evidence