N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide → 4-{4-[(2S)-3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-piperidin-1-yl}-N-(3,4-dimethoxy-phenyl)-benzenesulfonamide

HRID 351699Notes

Reaction equation

HRID 351699 reaction equation
[NH2:1][CH2:2][CH:3]([OH:19])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]3)=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>>[CH:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:3]([OH:19])[CH2:2][NH:1][CH:43]2[CH2:42][CH2:41][N:40]([C:37]3[CH:36]=[CH:35][C:34]([S:31]([NH:30][C:24]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=4)(=[O:32])=[O:33])=[CH:39][CH:38]=3)[CH2:45][CH2:44]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 12051790N-(3,4-dimethoxy-phenyl)-4-(4-oxo-piperidin-1-yl)-benzenesulfonamideHCID 148938061-Amino-3-(9H-carbazol-4-yloxy)-2-propanol

Product 1

HCID 120517944-{4-[(2S)-3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-piperidin-1-yl}-N-(3,4-dimethoxy-phenyl)-benzenesulfonamide

Procedure

The title compound was prepared from 1-Amino-3-(9H-carbazol-4-yloxy)-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 58-64° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.80-1.95 (m, 2H), 2.60-2.90 (m, 5H), 3.62 (s, 3H), 3.64 (s, 3H), 3.60-3.80 (m, 2H), 4.00-4.20 (m, 3H), 6.40-7.50 (m, 12H), 7.95 (s, 1H), 8.20 (d, 1H), 11.30 (s, 1H); MS (ES) m/z: 631.1 (MH+); HRMS Calcd. for C34H39N4O6S (MH+): 631.2590. Found: 631.2595.

Sources & evidence

ORD record
ord-065091f65f70484c8405d151c9780c25
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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