Trifluoroacetic acid → HCID 66931677, compound

Participants

Reaction Steps

A solution of 3-chloro-5-cyano-pyridine-2-carboxylic acid [3-((R)-5-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide (80 mg, 0.12 mmol) in dichloromethane (2 ml) was treated at room temperature with trifluoroacetic acid (0.89 ml, 1.16 mmol); the yellow solution immediately turned to orange. The reaction mixture was stirred at room temperature for 16 hours. For the workup, it was poured into a sodium carbonate solution (1 M, 2 ml), then extracted with dichloromethane (10 ml). The organic layer was washed with brine (5 ml), dried over sodium sulfate, and evaporated. After chromatography on silica gel using a gradient of dichloromethane and methanol=100/0 to 93/7 the 3-chloro-5-cyano-pyridine-2-carboxylic acid [3-((R)-5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide was obtained. For further purification the product was dissolved in dioxane and hydrochloric acid (4 N, 0.15 ml) was added. After evaporation at reduced pressure the salt was triturated in diethylether (2 ml), the solid material filtrated and dried. The title compound was obtained as a white solid (5 mg, 10% of theory). Mass (calculated) C18H15ClFN5O2.ClH [424.260]; (found) [M+H]+=388.

Provenance & Evidence