반응 #45678

반응 방정식

acetyl chloride

acetyl chloride

diisopropylethylamine

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

tetrahydrofuran

pyridine

→

compound

수율 17.0%

N-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}-N-methylacetamide

수율 17.0%

용매

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   온도by heating
3. 3
   온도under reflux for 1.5 hours
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGby stirring at 90° C. for 15 hours
6. 6
   온도After cooling
7. 7
   세척the organic layer was washed with saturated brine
8. 8
   건조The obtained organic layer was dried over anhydrous sodium sulfate
9. 9
   기타the solvent was evaporated away under reduced pressure
10. 10
    세척Elution with a mixed solvent of chloroform/methanol (10:1

실험 절차

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile (#53) (60 mg, 0.16 mmol) was dissolved in tetrahydrofuran (1.2 ml), and with cooling with ice, acetyl chloride (14 μl, 0.19 mmol) and diisopropylethylamine (38 μl, 0.22 mmol) were added, followed by stirring at room temperature for 2 hours. Further, acetyl chloride (14 μl, 0.19 mmol) was added, followed by heating under reflux for 1.5 hours. Since the reaction did not go on, pyridine (1.2 ml) was added, followed by stirring at 90° C. for 15 hours. After cooling followed by fractionation with water and ethyl acetate, the organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (10:1, v/v) gave the entitled compound (11 g, 0.03 mmol, 17%) as a brown oily substance.

출처