4-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide → 4-{[(Hexylamino)carbonyl]amino}-N-(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)benzenesulfonamide

HRID 1061376Notes

Reaction equation

HRID 1061376 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].C([O:41][C:42]1[CH:47]=[CH:46][C:45]([C@@H:48]([OH:51])[CH2:49][NH2:50])=[CH:44][C:43]=1[NH:52][S:53]([CH3:56])(=[O:55])=[O:54])C1C=CC=CC=1>>[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:50][CH2:49][C@H:48]([OH:51])[C:45]4[CH:46]=[CH:47][C:42]([OH:41])=[C:43]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:44]=4)[CH2:30][CH2:31]3)=[CH:24][CH:25]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=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 69654885N-[2-Benzyloxy-5-(2-amino-(1R)-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Product 1

HCID 696547834-{[(Hexylamino)carbonyl]amino}-N-(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)benzenesulfonamide

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 N-[2-benzyloxy-5-(2-amino-(1R)-1-hydroxy-ethyl)-phenyl]-methanesulfonamide (which was obtained in Example 8) according to the procedure of Example 255 as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=6.9 Hz, 3H), 1.20-1.80 (m, 10H), 1.95-2.15 (m, 2H), 2.50-3.30 (m, 7H), 2.97 (s, 3H), 3.55-3.70 (m, 2H), 4.70-4.85 (m, 1H), 5.90-6.10 (m, 1H), 6.48 (t, J=5.6 Hz, 1H), 6.83 (d, J=9.2 Hz, 2H), 6.90 (d, J=9.2 Hz, 2H), 6.91 (d, J=8.4 Hz, 1H), 7.07 (dd, J=8.4, 2.0 Hz, 1H), 7.24 (d, J=2.0 Hz, 1H), 7.46 (d, J=9.2 Hz, 2H), 7.51 (d, J=9.2 Hz, 1H), 8.50-8.90 (brs, 1H), 9.39 (s, 1H), 9.61 (s, 1H); MS (ES) m/z: 703.4 (MH+); HRMS Calcd. for C33H47N6O7S2 (MH+): 703.2948. Found: 703.2946.

Sources & evidence

ORD record
ord-0f2c567a11784432a76f0c2037361daf
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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