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

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

Reactant 3

HCID 6395Methanesulfonic Acid

HCID 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]+.