تفاعل #45789

معادلة التفاعل

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

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

→

compound

المردود 11.1%

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

المردود 11.1%

المذيبات

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction liquid
2. 2
   تركيزwas concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform (10 ml)
4. 4
   غسيلwashed with saturated brine (10 ml)
5. 5
   تجفيفAfter drying over anhydrous sodium sulfate and concentration
6. 6
   أخرىthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol-10:1)
7. 7
   أخرىthe eluate was purified in slurry with diethyl ether

الإجراء التجريبي

(3S)-3-(Dimethylamino)pyrrolidine (18.2 μl, 0.143 mmol) and triethylamine (26.7 μl, 0.191 mmol) were added to a dimethyl sulfoxide (0.5 ml) solution of 7-fluoro-2-hydroxymethyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-218) (27.0 mg, 0.096 mmol), followed by stirring in an oil bath at 95° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (10 ml), and washed with saturated brine (10 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol-10:1), and the eluate was purified in slurry with diethyl ether to obtain the entitled compound (4.00 mg, 11.1%) as a pale yellow solid.

المصدر