N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → N-(4-{4-[(2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)-5-(2-pyridinyl)-2-thiophenesulfonamide

HRID 1794886Notes

Reaction equation

HRID 1794886 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][CH:31]([C:33]1[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=1)[OH:32]>>[OH:32][CH:31]([C:33]1[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=1)[CH2:30][NH:29][CH:2]1[CH2:3][CH2:4][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:17])=[O:16])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 865845695-Pyridin-2-yl-thiophene-2-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide

Product 1

HCID 22220439N-(4-{4-[(2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)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 N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) 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), 2.45–2.75 (m, 5 H), 2.91 (s, 3 H), 3.40–3.60 (m, 2 H), 4.47 (dd, J=8.0, 4.1 Hz, 1 H), 6.80 (d, J=8.3 Hz, 1 H), 6.82 (d, J,=8.0 Hz, 2 H), 6.95 (d, J=8.0 Hz, 2 H), 7.00 (dd, J=8.3, 2.0 Hz, 1 H), 7.17 (d, J=2.0 Hz, 1 H), 7.37 (dd, J=4.8, 1.7 Hz, 1 H), 7.40(d, J=3.9 Hz, 1 H), 7.75 (d, J=3.9 Hz, 1 H), 7.88(dd, J=8.0, 1.7 Hz, 1 H), 7.98 (d, J=8.0 Hz, 1 H), 8.54 (brd, J=4.8 Hz, 1 H); MS (ES) m/z: 644.1 (MH+); HRMS Calcd. for C29H34N5O6S3 (MH+): 644.1671. Found: 644.1663.

Sources & evidence

ORD record
ord-1faea5a729254c6090dcff19cf7cce56
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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