N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → 4-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-N-(4-{4-[(2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)benzenesulfonamide

HRID 1794893Notes

Reaction equation

HRID 1794893 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]4)=[CH:21][CH:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[S:3]1.[NH2:32][CH2:33][CH:34]([C:36]1[CH:37]=[CH:38][C:39]([OH:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=1)[OH:35]>>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH2:30][CH2:29][CH:28]([NH:32][CH2:33][CH:34]([OH:35])[C:36]5[CH:37]=[CH:38][C:39]([OH:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=5)[CH2:27][CH2:26]4)=[CH:23][CH:24]=3)(=[O:16])=[O:17])=[CH:11][CH:10]=2)[S:3]1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 222205034-(2,4-Dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 222205484-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-N-(4-{4-[(2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)benzenesulfonamide

Procedure

The title compound was prepared from 4-(2,4-dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 231) 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 1.45–1.60 (m, 2 H), 1.85–2.05 (m, 2 H), 2.50–3.50 (m, 7 H), 2.93 (s, 3 H), 3.59 (brd, J=11.9 Hz, 2 H), 4.28 (dd, J=7.0, 3.8 Hz, 1 H), 4.60–4.65 (m, 1 H), 6.70–6.90 (m, 5 H), 7.05 (dd, J=8.3, 1.9 Hz, 1 H), 7.21 (d, J=1.9 Hz, 1 H), 7.33 (d, J=8.3 Hz, 2 H), 7.55 (d, J=8.3 Hz, 2 H); MS (ES) m/z: 690.0 (MH+); HRMS Calcd. for C30H36N5O8S3 (MH+): 690.1726. Found: 690.1714.

Sources & evidence

ORD record
ord-02fe6233d2594f0686a0ff8872c6a106
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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