Ammonium Acetate → HCID 67279764, compound

Participants

Reaction Steps

A mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (50 mg), ammonium acetate (68 mg), molecular sieves 4A (50 mg) and methanol (1.5 ml) was stirred at room temperature for four hours. Sodium cyanoborohydride (12 mg) was added to the reaction mixture, followed by stirring at room temperature for three days. The insoluble matter in the reaction mixture was removed by filtration through Celite, followed by washing with methanol (4 ml) twice. The filtrate was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for four hours. The reaction mixture was concentrated under reduced pressure. Diethyl ether (20 ml) was placed into the resulting residue, and the slurry was washed. Then, the solvent was removed by decantation. The resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (14.1 mg, 43%) as a solid.

Provenance & Evidence