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-octanesulfonamide

HRID 1794890Notes

Reaction equation

HRID 1794890 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][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH:26][C@@H:27]([CH2:40][NH2:41])[CH2:28][O:29][C:30]1[C:38]2[NH:37][C:36](=[O:39])[NH:35][C:34]=2[CH:33]=[CH:32][CH:31]=1>>[OH:26][C@H:27]([CH2:28][O:29][C:30]1[C:38]2[NH:37][C:36](=[O:39])[NH:35][C:34]=2[CH:33]=[CH:32][CH:31]=1)[CH2:40][NH:41][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][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[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 86584572Octane-1-sulfonic acid [4-(4-oxo-1-piperidineyl)-phenyl]-amide

Product 1

HCID 69654901N-{4-[4-({(2S)-2-Hydroxy-3-[(2-oxo-2,3-dihydro-1H-benzimidazol-4-yl)oxy]propyl}amino)-1-piperidineyl]phenyl}-1-octanesulfonamide

Procedure

The title compound was prepared from octane-1-sulfonic acid [4-(4-oxo-piperidin-1-yl)-phenyl]-amide (which was obtained in Example 230) 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 0.85(t, J=7.0 Hz, 3 H), 1.10–1.40 (m, 10 H), 1.50–1.70 (m, 4 H), 1.95–2.16 (m, 2 H), 2.67 (brt, J=11.1 Hz, 2 H), 2.93 (brt, J=7.9 Hz, 2 H), 2.95–3.20 (m, 3 H), 3.62–3.75 (m, 2 H), 4.00–4.12 (m, 2 H), 4.12–4.30 (m, 1 H), 6.59 (d, J=7.8 Hz, 1 H), 6.63 (d, J=8.3 Hz, 1 H), 6.80–7.00 (m, 3 H), 7.07 (d, J=9.0 Hz, 2 H), 9.33 (brs, 1 H), 10.60 (brs, 1 H), 10.75 (brs, 1 H); MS (ES) m/z: 574.1 (MH+); HRMS Calcd. for C29H44N5O5S (MH+): 574.3063. Found: 574.3084.

Sources & evidence

ORD record
ord-6516191207eb497caef163bf9bbbacaa
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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