Reacción #45602

Ecuación de reacción

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

Rendimiento 69.4%

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

Rendimiento 69.4%

Disolventes

dimethyl sulfoxide

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring at 90° C. for 8 hours
2. 2
   TemperaturaAfter cooling
3. 3
   Extracciónthis was extracted with ethyl acetate and chloroform
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe resulting residue was purified by silica gel column chromatography (chloroform:methanol-100:1)

Procedimiento

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.

Fuente