Reaction #157359

Reaction equation

tert-butyl 4-(2-chlorooxazole-4-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

aniline

potassium carbonate

→

title compound

Yield 48.8%

tert-butyl 4-(2-(phenylamino)oxazole-4-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Yield 48.8%

Solvents

THF

Conditions

Workup

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   OtherThe material was purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)

Procedure

A solution of tert-butyl 4-(2-chlorooxazole-4-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (117 mg, 0.277 mmol), aniline (51 mg, 0.554 mmol) and potassium carbonate (76 mg, 0.554 mmol) in THF (2 mL) was heated to 70° C. overnight. Upon cooling to rt, the reaction mixture was filtered and concentrated under reduced pressure. The material was purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient), yielding 64.8 mg (40%) of the title compound as the TFA salt. LC-MS: RT=6.72 min, [M+H]+=480.0.

Source