Trifluoroacetic acid → HCID 89922533, compound

Participants

Reaction Steps

TFA (4.5 mL) was added to a solution of tert-butyl 2-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)morpholine-4-carboxylate (252 mg, 0.575 mmol) in DCM (4.5 mL) at room temperature. After 0.5 hr, the solvent was removed. The residue in was dissolved in MeOH and this was applied onto an SCX column. After washing with MeOH, the product was eluted with 2N NH3 in MeOH to give 3-amino-4-chloro-5-(morpholin-2-yl)benzonitrile (132 mg) as an oil. This was dissolved in DCM (7 mL) and TEA (0.096 mL, 0.69 mmol) and BOC2O (0.16 mL, 0.69 mmol) were added. After stirring overnight, the solvent was removed and radial silica gel chromatography eluting with hexane containing 0 to 30% EtOAc afforded tert-butyl 2-(3-amino-2-chloro-5-cyanophenyl)morpholine-4-carboxylate (203 mg).

Provenance & Evidence