Methanesulfonic Acid → 5-[5-(1-Methanesulfonyl-piperidin-4-yl)-2-pyridin-4-yl-furan-3-yl]-indan-1-one oxime

HRID 271527Notes

Reaction equation

HRID 271527 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:40])[CH2:18][CH:19]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[C:33](=[N:37][O:38]C)[CH2:32][CH2:31]3)[C:20](=O)[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:55][S:56](O)(=[O:58])=[O:57]>>[CH3:55][S:56]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[O:40][C:20]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)=[C:19]([C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[C:33](=[N:37][OH:38])[CH2:32][CH2:31]4)[CH:18]=2)[CH2:15][CH2:16]1)(=[O:58])=[O:57]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 866001284-[3-(1-Methoxyimino-indan-5-yl)-4-oxo-4-pyridin-4-yl-butanoyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 1363419145-[5-(1-Methanesulfonyl-piperidin-4-yl)-2-pyridin-4-yl-furan-3-yl]-indan-1-one oximeYield 50%

Procedure

The product of Example 31, Step 3 (3.0 g, 5.5 mmol) was added to a stirred suspension of phosphorus pentoxide (8 g) in dry methane sulphonic acid (50 ml). After stirring at room temperature for 4 hours the reaction mixture was cautiously poured into a stirred solution of ice cold 50% aqueous sodium hydroxide (final pH 10). The mixture was extracted with chloroform, washed with water and brine, dried and concentrated in vacuo and the residue purified by silica gel chromatography to give the title compound (1.04 g, 50%); MS(ES+) m/e 466 [M+H]+.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-1c4f5612b281444bad9e0c9c1525fb56
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

Loading…