4-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide → 4-{[(Hexylamino)carbonyl]amino}-N-{4-[4-({(2S)-2-hydroxy-3-[(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl)oxy]propyl}amino)-1-piperidineyl]phenyl}benzenesulfonamide

HRID 1061392Notes

Reaction equation

HRID 1061392 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][C@H:36]([OH:51])[CH2:37][O:38][C:39]1[CH:48]=[CH:47][C:46]([OH:49])=[C:45]2[C:40]=1[CH2:41][CH2:42][C:43](=[O:50])[NH:44]2>>[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:34][CH2:35][C@H:36]([OH:51])[CH2:37][O:38][C:39]4[CH:48]=[CH:47][C:46]([OH:49])=[C:45]5[C:40]=4[CH2:41][CH2:42][C:43](=[O:50])[NH:44]5)[CH2:30][CH2:31]3)=[CH:22][CH:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)=[O:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 222203144-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamideHCID 69655051(S)-5-(3-amino-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 696549994-{[(Hexylamino)carbonyl]amino}-N-{4-[4-({(2S)-2-hydroxy-3-[(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl)oxy]propyl}amino)-1-piperidineyl]phenyl}benzenesulfonamide

Procedure

The title compound was prepared from 4-(3-hexyl-ureido)-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzensulfonamide (which was obtained in Example 225) and 5-(3-amino-(2S)-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one (which was obtained in Example 12) according to the procedure of Example 278 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=5.1 Hz, 3H), 1.20-1.35 (m, 8H), 1.35-1.50 (m, 2H), 1.75-1.90 (m, 2H), 2.39 (t, J=5.1 Hz, 2H), 2.50-2.75 (m, 5H), 2.82 (t, J=5.1 Hz, 2H), 3.05 (q, J=5.1 Hz, 2H), 3.40-3.55 (m, 2H), 3.75-3.85 (m, 3H), 4.90 (brs, 1H), 6.30 (t, J=5.1 Hz, 1H), 6.44 (d, J=6.6 Hz, 1H), 6.59 (d, J=6.6 Hz, 1H), 6.76 (d, J=6.9 Hz, 1H), 6.85 (d, J=6.9 Hz, 1H), 7.46 (d, J=6.9 Hz, 2H), 7.50 (d, J=6.9 Hz, 2H), 8.67 (s, 1H), 8.84 (s, 1H), 9.10 (brs, 1H), 9.50 (brs, 1H); MS (ES) m/z: 709.2 (MH+); HRMS Calcd. for C36H49N6O7S(MH+): 709.3383. Found: 709.3391.

Sources & evidence

ORD record
ord-549e128ad04f480fad0c5c8c99720199
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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