2,2-Difluoro-2-pyridin-2-ylethaneamine → HCID 178453010, compound

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Reaction Steps

A mixture of 3-cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-5-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide (103 mg, 0.225 mmol) and 2,2-difluoro-2-pyridin-2-yl-ethylamine (89 mg, 0.534 mmol) (Organic Process Research & Development 8:192-200, 2004), in DMSO (3 mL) was stirred for 18 hrs at 80° C. LC/MS (ESI) (M+H+ 580.2) indicated the formation of desired product. After removing most DMSO by high-vacuum rotary evaporation, water was added, after which time precipitate formed. The liquid was loaded onto a 5 g FisherBrand PrepSep SPE C18 cartridge. The solid was washed with water a few times. The washes were also loaded onto the cartridge. The cartridge was then washed with water (40 mL), acetonitrile (20 mL), mixture of acetonitrile/DCM (1:1, 20 mL) and DMF (10 mL). All organic washes were combined and stripped off solvent by rotary evaporation. An orange solid was obtained and used without further purification. LC/MS (ESI): M+H+ 580.1.

Provenance & Evidence