تفاعل #45714

معادلة التفاعل

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

المردود 27.0%

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

المردود 27.0%

المذيبات

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe system was purged with nitrogen
2. 2
   أخرىsealed up
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe solvent was evaporated away under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in chloroform
6. 6
   غسيلwashed with water
7. 7
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
8. 8
   أخرىthe solvent was evaporated away under reduced pressure
9. 9
   أخرىthe resulting residue was separated
10. 10
    أخرىpurified by preparative TLC
11. 11
    أخرىto obtain a main product
12. 12
    غسيلThis was washed with a mixed solvent of isopropyl ether and ethanol
13. 13
    ترشيحthe solid was collected by filtration

الإجراء التجريبي

(3S)-3-(Dimethylamino)pyrrolidine (53 μl, 0.42 mmol) and triethylamine (100 μl) were added to a dimethyl sulfoxide (2 ml) solution of 7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-166) (69 mg, 0.21 mmol). The system was purged with nitrogen, then sealed up, and heated at 110° C. for 3.5 hours. After cooling, the solvent was evaporated away under reduced pressure, the resulting residue was dissolved in chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was separated and purified by preparative TLC to obtain a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (24 mg, 27%) as a colorless solid.

المصدر