反応 #45602

反応方程式

Triethylamine

3-methylaminoazetidine hydrochloride trifluoroacetate

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

sodium bicarbonate water

3-methylaminoazetidine hydrochloride trifluoroacetate

triethylamine

→

compound

収率 69.4%

2-tert-Butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

収率 69.4%

溶媒

dimethyl sulfoxide

brine

反応条件

後処理

1. 1
   workup.STIRRINGby stirring at 90° C. for 8 hours
2. 2
   温度After cooling
3. 3
   抽出this was extracted with ethyl acetate and chloroform
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The resulting residue was purified by silica gel column chromatography (chloroform:methanol-100:1)

実験手順

Triethylamine (316 μl, 2.27 mmol) and 3-methylaminoazetidine hydrochloride trifluoroacetate (140 mg, 590 μmol) were added to a dimethyl sulfoxide (3.5 ml) solution of 2-tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-72) (140 mg, 454 μmol), followed by stirring overnight at 90° C., then 3-methylaminoazetidine hydrochloride trifluoroacetate (53.7 mg, 227 μmol) and triethylamine (63.3 μl, 454 μmol) were added, followed by stirring at 90° C. for 8 hours. After cooling, saturated sodium bicarbonate water and saturated brine were added to the reaction liquid, and this was extracted with ethyl acetate and chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol-100:1) to obtain the entitled compound (118 mg, 69%) as a pale yellow solid.

出典