Methanol → 3-{[6-(azetidin-1-ylcarbonyl)pyridin-3-yl]oxy}-5-hydroxy-N-(5-methylpyrazin-2-yl)benzamide

3-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide (Intermediate 2) (3.9 g, 7.9 mmol) was dissolved in ethyl acetate (200 mL) and ethanol (200 mL). 10% Palladium on carbon (390 mg, cat.) was added and the mixture stirred under an atmosphere of hydrogen for 16 hours. Methanol (150 mL) was added and the suspension was filtered. The filtrate was evaporated under reduced pressure. The residue was washed firstly with methanol (150 mL), ethyl acetate (150 mL) and DMA (10 mL) and secondly with DMF (50 mL). The combined filtrates were evaporated under reduced pressure to afford the product (3.17 g, 99%). 1H NMR δ (400 MHz, DMSO) 11.02 (s, 1H), 10.35 (s, 1H), 9.26 (s, 1H), 8.47 (s, 1H), 8.40 (s, 1H), 8.05 (d, 1H), 7.62 (d, 1H), 7.34 (s, 1H), 7.31 (s, 1H), 6.81 (s, 1H), 4.64 (t, 2H), 4.13 (t, 2H), 2.53 (s, 3H), 2.33 (quintet, 2H); m/z 406 (M+H)+.

1. filtrationthe suspension was filtered
2. customThe filtrate was evaporated under reduced pressure
3. washThe residue was washed firstly with methanol (150 mL), ethyl acetate (150 mL) and DMA (10 mL) and secondly with DMF (50 mL)
4. customThe combined filtrates were evaporated under reduced pressure

ORD 기록

ord-cce348f7f7f147c1beb484a228572f29

출처 데이터셋

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07902200B2