Trifluoroacetic acid → HCID 66931677, compound

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.

1. extractionextracted with dichloromethane (10 ml)
2. washThe organic layer was washed with brine (5 ml)
3. dry with materialdried over sodium sulfate
4. customevaporated

ORD record

ord-5f9eeaaf8e36444188391bf93bd9b219

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188079B2