Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86711711, compound

Participants

Reaction Steps

9-Methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid (450 mg, 1.14 mmol) was dissolved in dimethylacetamide (3 mL) and DIPEA (0.57 mL, 3.43 mmol). N,O-Dimethylhydroxylamine hydrochloride salt (123 mg, 1.26 mmol) was added to the solution, followed by dichloromethane (3 mL) and HATU (522 mg, 1.37 mmol). The reaction was stirred at room temperature for 1 hour. The crude reaction mixture was concentrated, diluted with 80 mL of dichloromethane, was washed with 2×50 mL of water and 3×50 mL of saturated potassium carbonate. The organic layer was collected, dried over magnesium sulfate, was filtered and was concentrated to afford N-methoxy-N,9-dimethyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxamide (quantitative yield) as an oil. 1H NMR (400 MHz, DMSO-d6): δ 10.84 (s, 1H), 8.32 (s, 1H), 7.18-7.12 (m, 1H), 6.96-6.88 (m, 3H), 5.38 (br s, 2H), 4.55 (tt, 1H), 3.76 (s, 3H), 3.75 (s, 3H), 3.49-3.09 (m, 5H), 2.40-2.23 (m, 2H), 1.83 (br d, 2H). MS (EI) for C21H24N8O3: 437 (MH+).

Provenance & Evidence