Реакция #45887

Уравнение реакции

2-Cyclopropyl-7-fluoro-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

Выход 46.1%

2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile

Выход 46.1%

Растворители

dimethyl sulfide

Условия реакции

Обработка

1. 1
   ТемператураAfter cooled
2. 2
   Концентрированиеthis was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with chloroform
4. 4
   Промывкаwashed with saturated brine
5. 5
   СушкаThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Другоеthe solvent was evaporated away under reduced pressure
7. 7
   ДругоеThe resulting residue was purified by preparative TLC (eluent, chloroform

Методика

2-Cyclopropyl-7-fluoro-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-315) (34 mg, 0.13 mmol) was dissolved in dimethyl sulfide (2 ml), then triethylamine (38 μl, 0.27 mmol) and (3S)-3-(dimethylamino)pyrrolidine (36 μl, 0.28 mmol) were added, followed by stirring under nitrogen atmosphere at 90° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (21 mg, 25%) as a brown crystal.

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