N,N-Dimethylglycine → 5-{5-[1-(2-Dimethylamino-ethanoyl)-piperidin-4-yl]-2-pyridin-4-yl-furan-3-yl}-indan-1-one oxime

HRID 271528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271528
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[C:9]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23](=O)[CH2:22][CH2:21]4)[CH:8]=2)[CH2:3][CH2:2]1.O.[OH:29][N:30]1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:46][N:47]([CH2:49][C:50]([OH:52])=O)[CH3:48]>CN(C=O)C>[CH3:46][N:47]([CH3:48])[CH2:49][C:50]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[C:9]([C:18]3[CH:26]=[C:25]4[C:24](=[CH:20][CH:19]=3)[C:23](=[N:30][OH:29])[CH2:22][CH2:21]4)[CH:8]=2)[CH2:3][CH2:2]1)=[O:52]

Komponenten

6

Edukt 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 693146085-(5-Piperidin-4-yl-2-pyridin-4-yl-furan-3-yl)-indan-1-one

Produkt 1

HCID 1363552535-{5-[1-(2-Dimethylamino-ethanoyl)-piperidin-4-yl]-2-pyridin-4-yl-furan-3-yl}-indan-1-one oximeAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the product from Example 31 Step 5 (0.17 g, 0.47 mmol), N-cyclohexylcarbodiimide,N′-methyl polystyrene resin (0.4 g, 0.65 mmol, 1.7 mmol/g), and 1-hydroxybenzotriazole hydrate (0.081 g, 0.6 mmol) were suspended in DMF (4 ml) and treated with triethylamine (0.084 ml, 0.6 mmol) and dimethylamino-acetic acid (0.048 g, 0.47 mmol). The reaction was stirred at room temperature for 16 hours and filtered on to a 10 g SCX cartridge (Varian Mega Bond Elute). The cartridge was then washed with methanol and then a 1:90.880 ammonia:methanol solution. The ammonia containing fractions were then reduced in vacuo and the residue purified by chromatography on silica gel eluting with a mixture of 0.880 ammonia/methanol/chloroform (0.5:4.5:95) to afford the title compound (0.097 g, 47%); MS (ES+) m/e 444 (M+H)+.

Aufarbeitung

  1. filtrationfiltered on to a 10 g SCX cartridge (Varian Mega Bond Elute)
  2. washThe cartridge was then washed with methanol
  3. customthe residue purified by chromatography on silica gel eluting with a mixture of 0.880 ammonia/methanol/chloroform (0.5:4.5:95)

Quellen und Nachweise

ORD-Eintrag
ord-91602fe5b292464596a6dd3e26314c35
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452906B2

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