4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → N-[4-(4-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino}-1-piperidineyl)phenyl]-5-(2-pyridinyl)-2-thiophenesulfonamide

HRID 1794885Notes

Reaction equation

HRID 1794885 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]([C:18]3[S:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:21][CH:22]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:29][CH2:30][C@H:31]([OH:41])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1>>[OH:41][C@H:31]([CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)[CH2:30][NH:29][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([C:18]3[S:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:21][CH:22]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 865845695-Pyridin-2-yl-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide

Product 1

HCID 69654648N-[4-(4-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino}-1-piperidineyl)phenyl]-5-(2-pyridinyl)-2-thiophenesulfonamide

Procedure

The title compound was prepared from 5-pyridin-2-yl-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide (which was obtained in Example 227) and 4-((2S)-3-amino-2-hydroxy-propoxy)-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 1.20–1.40 (m, 2 H), 1.80–1.90 (m, 2 H), 2.40–2.80 (m, 5 H), 3.50–3.60 (m, 2 H), 3.70–3.90 (m, 3 H), 4.99 (brs, 1 H), 6.66 (d, J=8.0 Hz, 2 H), 6.75 (d, J=8.0 Hz, 2 H), 6.83 (d, J=9.0 Hz, 2 H), 6.96 (d, J=9.0 Hz, 1 H), 7.36 (dd, J=4.4, 1.7 Hz, 1 H), 7.41 (d, J=4.0 Hz, 1 H), 7.76 (d, J=4.0 Hz, 1 H), 7.88 (dd, J=8.0, 1.7 Hz, 1 H), 8.00(d, J=8.0 Hz, 1 H), 8.54 (d, J=4.4 Hz, 1 H), 8.89 (s, 1 H); MS (ES) m/z: 580.9 (MH+); HRMS Calcd. for C29H33N4O5S2 (MH+): 581.1892. Found: 581.1910.

Sources & evidence

ORD record
ord-eeebd34498044bff9c8b584c42b86aba
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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