反应详情

Trifluoroacetic acid (1 ml) was added to a dichloromethane (2 ml) solution of tert-butyl N-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-β-alaninate (I-279) (51 mg, 0.104 mmol), followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in dichloromethane (1 ml), and at room temperature, thionyl chloride (10 μl, 0.138 mmol) was added, followed by stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, the then dissolved in chloroform, and washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine. After drying over anhydrous sodium sulfate and concentration, the insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1, v/v), the eluate was purified in slurry with diethyl ether to obtain the entitled compound (8.00 mg, 17%) as a pale yellow solid.

1. customThe reaction liquid
2. concentrationwas concentrated under reduced pressure
3. dissolutionthe residue was dissolved in dichloromethane (1 ml)
4. stirringby stirring at room temperature for 1 hour
5. customThe reaction liquid
6. concentrationwas concentrated under reduced pressure
7. dissolutionthe then dissolved in chloroform
8. washwashed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
9. dry with materialAfter drying over anhydrous sodium sulfate and concentration
10. customthe insoluble matter was separated by filtration
11. customthe solvent was evaporated away
12. customthe resulting residue was purified by preparative TLC (eluent, chloroform
13. custommethanol=20:1, v/v), the eluate was purified in slurry with diethyl ether