反应详情

tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate (I-328) (92.0 mg, 0.403 mmol) was dissolved in dichloromethane (1 ml), and at room temperature, trifluoroacetic acid (1 ml) was added, followed by stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in dimethyl sulfoxide (2 ml), then triethylamine (84.2 μl, 0.604 mmol) and 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (118 mg, 0.403 mmol) was added, followed by stirring in an oil bath at 100° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (32.0 mg, 20%) as a colorless oily substance.

1. customThe reaction liquid
2. concentrationwas concentrated under reduced pressure
3. dissolutionthe residue was dissolved in dimethyl sulfoxide (2 ml)
4. stirringby stirring in an oil bath at 100° C. for 5 hours
5. customThe reaction liquid
6. concentrationwas concentrated under reduced pressure
7. dissolutionthe residue was dissolved in ethyl acetate
8. washwashed with water and saturated brine
9. dry with materialAfter drying over anhydrous sodium sulfate
10. customthe insoluble matter was separated by filtration
11. customthe residue obtained by concentration
12. customwas purified by preparative TLC (eluent, chloroform