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

HRID 1061384Notes

Reaction equation

HRID 1061384 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]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH:22][C@@H:23]([CH2:36][NH2:37])[CH2:24][O:25][C:26]1[C:34]2[NH:33][C:32](=[O:35])[NH:31][C:30]=2[CH:29]=[CH:28][CH:27]=1>>[OH:22][C@H:23]([CH2:24][O:25][C:26]1[C:34]2[NH:33][C:32](=[O:35])[NH:31][C:30]=2[CH:29]=[CH:28][CH:27]=1)[CH2:36][NH:37][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 86584570N-[4-(4-Oxo-1-piperidinyl)phenyl]-1-butanesulfonamide

Product 1

HCID 69654812N-{4-[4-({(2S)-2-Hydroxy-3-[(2-oxo-2,3-dihydro-1H-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]phenyl}-1-butanesulfonamide

Procedure

The title compound was prepared from butane-1-sulfonic acid [4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 228) 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 255 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.83 (t, J=7.2 Hz, 3H), 1.20-1.70 (m, 6H), 1.95-2.10 (m, 2H), 2.67 (brt, J=11.7 Hz, 2H), 2.70-3.20 (m, 7H), 3.62-3.75 (m, 2H), 3.95-4.10 (m, 3H), 6.59 (d, J=7.5 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 6.80-7.00 (m, 3H), 7.06 (d, J=9.0 Hz, 2H), 9.32 (brs, 1H), 10.61 (brs, 1H), 10.73 (brs, 1H); MS (ES) m/z: 518.1 (MH+); HRMS Calcd. for C25H36N5O5S(MH+): 518.2437. Found: 518.2452.

Sources & evidence

ORD record
ord-df2c732635154a8a912f6cf3b84dd665
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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