N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide → 4-{4-[(2S)-3-(4-Benzyloxy-phenoxy)-2-hydroxy-propylamino]-piperidin-1-yl}-N-(3,4-dimethoxy-phenyl)-benzenesulfonamide

HRID 351698Notes

Reaction equation

HRID 351698 reaction equation
[NH2:1][CH2:2][CH:3]([OH:20])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([N:41]3[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]3)=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C@@H:3]([OH:20])[CH2:2][NH:1][CH:44]2[CH2:43][CH2:42][N:41]([C:38]3[CH:37]=[CH:36][C:35]([S:32]([NH:31][C:25]4[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=4)(=[O:33])=[O:34])=[CH:40][CH:39]=3)[CH2:46][CH2:45]2)=[CH:7][CH:8]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 12051790N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamideHCID 120517911-Amino-3-[4-(benzyloxy)phenoxy]-2-propanol

Product 1

HCID 101897324-{4-[(2S)-3-(4-Benzyloxy-phenoxy)-2-hydroxy-propylamino]-piperidin-1-yl}-N-(3,4-dimethoxy-phenyl)-benzenesulfonamide

Procedure

The title compound was prepared from 1-Amino-3-(4-benzyloxy-phenoxy)-propan-2-ol and Reference Example 73, N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide, according to the procedure of Example 1 as an off-white solid; mp 113-121° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.15-1.35 (m, 2H), 1.75-1.90 (m, 2H), 2.50-2.90 (m, 5H), 2.89 (s, 3H), 3.61 (s, 3H), 3.64 (s, 3H), 3.64-3.80 (m, 5H), 5.02 (s, 2H), 6.70-7.00 (m, 9H), 7.30-7.70 (m, 7H); MS (ES) m/z: 648.1 (MH+); HRMS Calcd. for C35H42N3O7S (MH+): 648.2743. Found: 648.2710.

Sources & evidence

ORD record
ord-85bb16aafaea4009a864e1a40ba81acd
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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