تفاعل #45646

معادلة التفاعل

ethyl acetate

triethylamine

Ethyl-4-cyan-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

(3S)-3-(dimethylamino)pyrrolidine

→

compound

المردود 7.0%

Ethyl-4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

المردود 7.0%

المذيبات

brine

dimethyl sulfoxide

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added all at a time
2. 2
   درجة الحرارةThe mixture liquid was cooled to room temperature
3. 3
   أخرىThe aqueous layer was separated
4. 4
   استخلاصthis was extracted twice with ethyl acetate
5. 5
   غسيلwashed with saturated brine
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   أخرىThe insoluble matter was separated by filtration
8. 8
   أخرىthe solvent was evaporated away
9. 9
   أخرىthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2)

الإجراء التجريبي

Ethyl-4-cyan-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate 111) (200 mg, 0.62 mmol) was dissolved in dimethyl sulfoxide (12 ml), and at room temperature, triethylamine (112 μl, 0.80 mmol) was added. Next, the solution was heated at 150° C., and a solution of (3S)-3-(dimethylamino)pyrrolidine (94 μl, 0.74 mmol) dissolved in dimethyl sulfoxide (2 ml) was added all at a time, followed by further stirring for 1 hour. The mixture liquid was cooled to room temperature, then this was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, this was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=98:2) to obtain the entitled compound (17.5 mg, 7%) as a yellow powdery crystal.

المصدر