Triethylamine → 4-fluoro-N-(4-methoxy-7-phenyl-benzooxazol-2-yl)-benzamide

To a stirred solution of 100 mg (0.42 mmol) 4-methoxy-7-phenyl-benzooxazol-2-ylamine, 0.087 ml (0.62 mmol) triethylamine and 5.1 mg N,N-dimethyl-4-aminopyridine in 5 ml THF at room temperature was added dropwise a solution of 0.064 ml (0.54 mmol) 4-fluoro-benzoyl chloride in 2 ml THF and stirring continued at 65° C. for 16 h. The reaction mixture was then concentrated in vacuo. To the residue was added water, and the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4 then 4/1 ethyl acetate/hexane) followed by trituration in ether afforded 50 mg (33%) 4-fluoro-N-(4-methoxy-7-phenyl-benzooxazol-2-yl)-benzamide as a light yellow crystalline solid. EI-MS m/e (%): 362 (M+, 90), 123 ([FC6H4CO+, 100).

1. concentrationThe reaction mixture was then concentrated in vacuo
2. additionTo the residue was added water
3. extractionthe mixture was extracted three times with dichloromethane
4. dry with materialThe combined organic phases were dried over sodium sulfate
5. concentrationconcentrated in vacuo

ORD-Eintrag

ord-1fd4ea1107d8442d928b518260862d19

Quelldatensatz

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06992083B2