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

HRID 271525

반응식

HRID 271525 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-42944ea4f34f411cacf759b93aef9564
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452906B2

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