HCID 10863584, compound → HCID 10277568, compound

HRID 1595673Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:31](O)=[O:32])[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH:34][NH:35]C(C1CCN(CC2C=CC(C3C=CC=CN=3)=CC=2)C(S(C2C=CC(OC)=CC=2)(=O)=O)C1)=O>>[OH:34][NH:35][C:31]([C:12]1([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:10])=[O:11])[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:23][CH:24]=2)[CH2:14][CH2:13]1)=[O:32]

Participants

Reactant 2

HCID 10863584HCID 10863584, compound

HCID 86757374HCID 86757374, compound

Product 1

HCID 10277568HCID 10277568, compoundYield 33%

Procedure

Starting from 4-(4-methoxy-benzenesulfonyl)-1-(4pyridin-2-yl-benzyl)-piperidine-4-carboxylic acid (1.32 g, 2.83 mmol) and following the procedure outlined in example 83, 480 mg of 4-(4-methoxy-benzenesulfonyl-1-(4pyridin-2-yl-benzyl)-piperidine-4-carboxylic acid hydroxyamide was isolated as a HCl salt, a white powder. Yield 33%; mp 214° C.; MS: 482.0 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ2.30 (m, 2H), 2.80 (m, 2H), 3.42 (d, J=12.5 Hz, 2H), 3.75 (m, 2H), 3.88 (s, 3H), 4.36 (s, 2H), 7.15 (d, J=8.9 Hz, 2H), 7.59-7.74 (m, 4H), 7.84-7.95 (m, 3H), 8.55 (d, J=8.1 Hz, 1H), 8.79 (s, 1H), 9.14 (s, 1H), 10.68 (s, 1H), 11.17 (s, 1H)

Sources & evidence

ORD record: ord-860d4e28d0be470897b6ae0ad28e2d58
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288086B1

Reaction notes

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