تفاعل #45678

معادلة التفاعل

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

المردود 17.0%

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

المردود 17.0%

المذيبات

ethyl acetate

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   درجة الحرارةby heating
3. 3
   درجة الحرارةunder reflux for 1.5 hours
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGby stirring at 90° C. for 15 hours
6. 6
   درجة الحرارةAfter cooling
7. 7
   غسيلthe organic layer was washed with saturated brine
8. 8
   تجفيفThe obtained organic layer was dried over anhydrous sodium sulfate
9. 9
   أخرىthe solvent was evaporated away under reduced pressure
10. 10
    غسيلElution with a mixed solvent of chloroform/methanol (10:1

الإجراء التجريبي

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.

المصدر