4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → N-[4-(4-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino}-1-piperidineyl)phenyl]-1-octanesulfonamide

HRID 1061391Notes

Reaction equation

HRID 1061391 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:26][CH2:27][C@H:28]([OH:38])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1>>[OH:38][C@H:28]([CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)[CH2:27][NH:26][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 86584572Octane-1-sulfonic acid [4-(4-oxo-1-piperidineyl)-phenyl]-amide

Product 1

HCID 69654849N-[4-(4-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino}-1-piperidineyl)phenyl]-1-octanesulfonamide

Procedure

The title compound was prepared from octane-1-sulfonic acid (4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 230) and 4-((2S)-3-amino-2-hydroxy-propoxyl)-phenol (which was obtained in Example 5) according to the procedure of Example 278 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.85 (t, J=7.0 Hz, 3H), 1.15-1.45 (m, 12H), 1.50-1.70 (m, 2H), 1.80-1.95 (m, 2H), 2.50-2.80 (m, 5H), 2.92 (brt, J=6.7 Hz, 2H), 3.54 (brd, J=12.3 Hz, 2H), 3.70-3.90 (m, 3H), 6.66 (d, J=6.7 Hz, 2H), 6.75 (d, J=8.3 Hz, 1H), 6.88 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 8.89 (brs, 1H), 9.28 (brs, 1H); MS (ES) m/z: 534.1 (MH+); HRMS Calcd. for C28H44N3O5S(MH+): 534.3002. Found: 534.3017.

Sources & evidence

ORD record
ord-65b8065a36b5471c9cf65a13bb11fc42
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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