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

HRID 600529
ノート
印刷プレビュー

反応式

HRID 600529 の反応式
[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([O:30]CC4C=CC=CC=4)[CH:29]=3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=3)=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.CO>C(OCC)(=O)C.C(O)C.[Pd]>[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([OH:30])[CH:29]=3)[C:17]([NH:19][C:20]3[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=3)=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 887MethanolHCID 536297003-{[6-(Azetidin-1-ylcarbonyl)pyridin-3-yl]oxy}-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide2 回

生成物 1

HCID 536296993-{[6-(azetidin-1-ylcarbonyl)pyridin-3-yl]oxy}-5-hydroxy-N-(5-methylpyrazin-2-yl)benzamide収率 99%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-cce348f7f7f147c1beb484a228572f29
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902200B2

反応ノート

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