Acetic Acid → 5-{5-[1-(2-Methoxyethyl)-piperidin-4-yl]-2-pyridin-4-yl-furan-3-yl}-indan-1-one oxime

HRID 271525

反応式

HRID 271525 の反応式
[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](=[N:27][OH:28])[CH2:22][CH2:21]4)[CH:8]=2)[CH2:3][CH2:2]1.[CH3:29][O:30][CH2:31][CH:32]=O.C([BH3-])#N.C[NH+](C)C.C(O)(=O)C>CO>[CH3:29][O:30][CH2:31][CH2:32][N:1]1[CH2:2][CH2:3][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:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23](=[N:27][OH:28])[CH2:22][CH2:21]4)[CH:8]=2)[CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 91563MethoxyacetaldehydeHCID 131727185Trimethylammonium cyanoborohydrideHCID 1363419135-(5-Piperidin-4-yl-2-pyridin-4-yl-furan-3-yl)-indan-1-one oxime

生成物 1

HCID 1363419125-{5-[1-(2-Methoxyethyl)-piperidin-4-yl]-2-pyridin-4-yl-furan-3-yl}-indan-1-one oxime収率 60%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of the product of Example 31 (0.149 g, 0.4 mmol), methoxy-acetaldehyde (0.037 g, 0.5 mmol) (E. M. Acton et al, J. Med. Chem., 1986, 29, 2074) and polymer bound trimethylammonium cyanoborohydride (200 mg, 0.8 mmol, 4 mmol/g) in methanol (5 ml) containing acetic acid (0.2 ml) was stirred at room temperature for 24 hours. The reaction mixture was then filtered and the resin washed with methanol. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography eluting with a 1:9:90 mixture of 0.880 ammonia solution:ethanol:chloroform to give the title compound (0.103 g, 60%); MS(ES+) m/e 432 [M+H]+.

後処理

  1. filtrationThe reaction mixture was then filtered
  2. washthe resin washed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by silica gel chromatography
  5. washeluting with a 1:9:90 mixture of 0.880 ammonia solution

出典と根拠

ORDレコード
ord-42944ea4f34f411cacf759b93aef9564
出典データセット
uspto-grants-2008_11
特許番号
US07452906B2

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