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

HRID 1794880Notes

Reaction equation

HRID 1794880 reaction equation
[CH2:1]([NH:7][C:8](=[O:33])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:34][C@@H:35]([CH2:48][NH2:49])[CH2:36][O:37][C:38]1[C:46]2[NH:45][C:44](=[O:47])[NH:43][C:42]=2[CH:41]=[CH:40][CH:39]=1>>[CH2:1]([NH:7][C:8]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:27][CH2:28][CH:29]([NH:49][CH2:48][C@H:35]([OH:34])[CH2:36][O:37][C:38]4[C:46]5[NH:45][C:44](=[O:47])[NH:43][C:42]=5[CH:41]=[CH:40][CH:39]=4)[CH2:30][CH2:31]3)=[CH:22][CH:21]=2)(=[O:17])=[O:18])=[CH:12][CH:11]=1)=[O:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 222203144-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 696547544-{[(Hexylamino)carbonyl]amino}-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-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 225) 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 a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=6.8 Hz, 3 H), 1.20–1.60 (m, 10 H), 1.90–2.05 (m, 2 H), 2.50–3.50 (m, 9 H), 3.50–3.65 (m, 1 H), 3.95–4.05 (m, 2 H), 6.43 (t, J=5.6 Hz, 1 H), 6.58 (d, J=7.8 Hz, 1 H), 6.61 (d, J=8.2 Hz, 1 H), 6.70–6.89 (m, 5 H), 7.46(d, J=9.0 Hz, 2 H), 7.51(d, J=9.0 Hz, 2 H), 9.06 (s, 1 H), 9.60 (brs, 1 H), 10.60 (s, 1 H), 10.75 (s, 1 H); MS (ES) m/z: 680.3 (MH+); HRMS Calcd. for C34H46N7O6S (MH+): 680.3230. Found: 680.3221.

Sources & evidence

ORD record
ord-b69094e31ed24ba786055c97208eadee
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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