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

HRID 1794891Notes

Reaction equation

HRID 1794891 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]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=4)(=[O:25])=[O:24])=[CH:21][CH:22]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:36][CH2:37][C@H:38]([OH:48])[CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1>>[OH:48][C@H:38]([CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1)[CH2:37][NH:36][CH: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]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][N:27]=4)(=[O:25])=[O:24])=[CH:21][CH:22]=3)(=[O:16])=[O:17])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 865845715-(5-Trifluoromethyl-pyridin-2-sulfonyl)-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide

Product 1

HCID 69654929N-[4-(4-{[(2S)-2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino}-1-piperidineyl)phenyl]-5-{[5-(trifluoromethyl)-2-pyridinyl]sulfonyl}-2-thiophenesulfonamide

Procedure

The title compound was prepared from 5-(5-trifluoromethyl-pyridine-2-sulfonyl)-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide (which was obtained in Example 229) and 4-((2S)-3-amino-2-hydroxy-propoxyl)-phenol (which was obtained in Example 5) according to the procedure of Example 278 as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.25–1.45 (m, 2 H), 1.70–1.95 (m, 2 H), 2.50–2.85 (m, 5 H), 3.54 (brd, J=12.4 Hz, 2 H), 3.65–3.95 (m, 3 H), 6.60–6.90 (m, 8 H), 7.92 (d, J=1.6 Hz, 1 H), 8.41 (d, J=8.3 Hz, 1 H), 8.48 (d, J=1.6 Hz, 1 H), 8.61 (dd, J=8.3, 2.0 Hz, 1 H), 8.89 (s, 1 H), 9.23 (s, 1 H); MS (ES) m/z: 713.1 (MH+); HRMS Calcd. for C30H32F3N4O7S3 (MH+): 713.1385. Found: 713.1407.

Sources & evidence

ORD record
ord-07836308520041f489d3ce81aab33dbb
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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