4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → N-(3,4-Dimethoxy-phenyl)-4-{4-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzenesulfonamide

HRID 351700Notes

Reaction equation

HRID 351700 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][CH:37]([NH:1][CH2:2][C@H:3]([OH:13])[CH2:4][O:5][C:6]4[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=4)[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 12051790N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide

Product 1

HCID 10120294N-(3,4-Dimethoxy-phenyl)-4-{4-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzenesulfonamide

Procedure

The title compound was prepared from 4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol 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 101-106° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.15-1.30 (m, 2H), 1.70-1.90 (m, 2H), 2.50-2.90 (m, 5H), 3.61 (s, 3H), 3.63 (s, 3H), 3.60-3.90 (m, 5H), 6.45 (dd, 1H), 6.60-6.80 (m, 8H), 6.90 (d, 1H), 7.45 (d, 1H); MS (ES) m/z: 557.9 (MH+); HRMS Calcd. for C28H36N3O7S (MH+): 558.2274. Found: 558.2293.

Sources & evidence

ORD record
ord-1df5489cdd334bd1857be55efc1035e7
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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