N,N-Dimethylglycine → HCID 59506965, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (153 mg, 0.344 mmol) produced in Example C12(iv), N,N-dimethylglycine (79.5 mmol, 0.771 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (321 mg, 0.843 mmol) and pyridine (3 mL) was stirred at 100° C. for 15 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (5 mL), and the mixture was extracted with ethyl acetate (5 mL×4). The organic layers were combined, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and crystallized from diisopropyl ether/ethyl acetate to give the title compound (25.4 mg, 14%) as pale-orange crystals.

Provenance & Evidence