2-Amino-1-(6-methylpyridin-3-yl)ethanol → 4-{[(Hexylamino)carbonyl]amino}-N-[4-(4-{[2-hydroxy-2-(6-methyl-3-pyridinyl)ethyl]amino}-1-piperidineyl)phenyl]benzenesulfonamide
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].[NH2:34][CH2:35][CH:36]([C:38]1[CH:39]=[N:40][C:41]([CH3:44])=[CH:42][CH:43]=1)[OH:37]>>[CH2:1]([NH:7][C:8]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:27][CH2:28][CH:29]([NH:34][CH2:35][CH:36]([OH:37])[C:38]4[CH:39]=[N:40][C:41]([CH3:44])=[CH:42][CH:43]=4)[CH2:30][CH2:31]3)=[CH:24][CH:25]=2)(=[O:18])=[O:17])=[CH:14][CH:15]=1)=[O:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
3
Procedure
The title compound was prepared from 4-(3-hexyl-ureido)-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 225) and 2-amino-1-(6-methyl-pyridin-3-yl)ethanol according to the procedure of Example 255 as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=6.8 Hz, 3H), 1.20-3.30 (m, 19H), 2.45 (s, 3H), 3.50-3.75 (m, 2H), 4.70-4.80 (m, 1H), 6.41 (t, J=5.5 Hz, 1H), 6.78 (d, J=9.1 Hz, 2H), 6.87 (d, J=9.1 Hz, 2H), 7.21 (d, J=8.0 Hz, 1H), 7.46 (d, J=9.2 Hz, 2H), 7.48 (d, J=9.2 Hz, 2H), 7.64 (dd, J=8.0, 2.0 Hz, 1H), 8.43 (d, J=2.0 Hz, 1H), 9.00 (s, 1H), 9.50 (brs, 1H), 11.10 (s, 1H); MS (ES) m/z: 609.3 (MH+); HRMS Calcd. for C32H45N6O4S(MH+): 609.3223. Found: 609.3235.
Sources & evidence
- ORD record
- ord-25fc1bbd7ea641f8b3be204fa08ad901
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
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