3-Amino-2-pyrazinecarboxylic acid → 3-amino-N-(4-fluoro-2-hydroxyphenyl)pyrazine-2-carboxamide

The tert-butyl 4-[4-[5-amino-6-(6-fluoro-1,3-benzoxazol-2-yl)pyrazin-2-yl]pyrazol-1-yl]piperidine-1-carboxylate used as starting material was prepared as follows: 3-aminopyrazine-2-carboxylic acid (5 g) and 2-amino-5-fluoro-phenol (5.94 g) were dissolved in DMF (30 ml). Triethylamine (5.81 g) and HATU (19.13 g) were added to the solution. The resulting mixture was stirred at room temperature for 24 hours, diluted with ethyl acetate (100 ml) and washed with brine (3×20 ml). The organic layer was dried over sodium sulfate. The precipitate was collected, recrystallized in ethanol and further purified by chromatography on silica gel (hexane/ethyl acetate/Methanol) to give 3-amino-N-(4-fluoro-2-hydroxy-phenyl)pyrazine-2-carboxamide (6 g). NMR Spectrum: (400 MHz, DMSOd6) 10.8 (s, 1H), 10.2 (s, 1H), 8.30 (m, 2H), 7.80 (s, 1H), 7.50 (br, 2H), 6.60 (m, 2H). Mass spectrum: M+H+ 249.

1. customwas prepared
2. washwashed with brine (3×20 ml)
3. dry with materialThe organic layer was dried over sodium sulfate
4. customThe precipitate was collected
5. customrecrystallized in ethanol
6. customfurther purified by chromatography on silica gel (hexane/ethyl acetate/Methanol)

ORD 기록

ord-9394b6aa5817401182d05fa1caa06630

출처 데이터셋

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08017611B2