4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 4-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-N-{4-[4-({(2S)-2-hydroxy-3-[(2-oxo-2,3-dihydro-1H-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]phenyl}-benzenesulfonamide

HRID 1061388Notes

Reaction equation

HRID 1061388 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.[OH:32][C@@H:33]([CH2:46][NH2:47])[CH2:34][O:35][C:36]1[C:44]2[NH:43][C:42](=[O:45])[NH:41][C:40]=2[CH:39]=[CH:38][CH:37]=1>>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][CH:28]([NH:47][CH2:46][C@H:33]([OH:32])[CH2:34][O:35][C:36]5[C:44]6[NH:43][C:42](=[O:45])[NH:41][C:40]=6[CH:39]=[CH:38][CH:37]=5)[CH2:27][CH2:26]4)=[CH:21][CH:20]=3)(=[O:16])=[O:17])=[CH:13][CH:14]=2)[S:3]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 222205034-(2,4-Dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 865845734-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]-N-{4-[4-({(2S)-2-hydroxy-3-[(2-oxo-2,3-dihydro-1H-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]phenyl}-benzenesulfonamide

Procedure

The title compound was prepared from 4-(2,4-dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 231) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (U.S. Pat. No. 5,786,356/1998) according to the procedure of Example 278 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.60 (m, 2H), 1.90-2.10 (m, 2H), 2.50-2.70 (m, 2H), 2.70-3.50 (m, 5H), 3.60 (brd, J=11.6 Hz, 2H), 4.00 (brs, 3H), 4.60 (dd, J=9.4, 4.2 Hz, 1H), 6.58 (d, J=7.8 Hz, 1H), 6.62 (d, J=8.1 Hz, 1H), 6.70-6.90 (m, 5H), 7.35 (d, J=8.4 Hz, 2H), 7.55 (d, J 8.4 Hz, 2H), 9.70 (brs, 1H), 10.61 (brs, 1H), 10.72 (brs, 1H); MS (ES) m/z: 667.0 (MH+); HRMS Calcd. for C31H35N6O7S2 (MH+): 677.2009. Found: 677.1999.

Sources & evidence

ORD record
ord-54ef8dcec5f241e4b49472c32754905a
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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