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

HRID 271525

Reaction equation

HRID 271525 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-42944ea4f34f411cacf759b93aef9564
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Linked notes

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