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

HRID 600529
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600529
[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
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Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator
HCID 702
Ethanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cce348f7f7f147c1beb484a228572f29
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902200B2

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