반응 #45857

반응 방정식

(3S)-3-(Ethylamino)pyrrolidine

triethylamine

2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

수율 23.5%

2-Cyclopropyl-7-[(3S)-3-(ethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 23.5%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   기타The reaction liquid
2. 2
   농축was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   세척washed with water and saturated brine
5. 5
   건조After drying over anhydrous sodium sulfate
6. 6
   기타the insoluble matter was separated by filtration
7. 7
   기타the residue obtained by concentration
8. 8
   기타was purified by preparative TLC (eluent, chloroform
9. 9
   기타methanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether

실험 절차

(3S)-3-(Ethylamino)pyrrolidine (85 μl, 0.684 mmol) and triethylamine (95 μl, 0.684 mmol) were added to a dimethyl sulfoxide (2 ml) solution of 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (100 mg, 0.342 mmol), followed by stirring in an oil bath at 95° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, then 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, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether to obtain the entitled compound (31.0 mg, 23%) as a white solid.

출처