4-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide → N-[4-(4-{[(2R)-2-(3-Chlorophenyl)-2-hydroxyethyl]amino}-1-piperidineyl)phenyl]-4-{[(hexylamino)carbonyl]amino}benzenesulfonamide

HRID 1061396Notes

Reaction equation

HRID 1061396 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].Cl.[NH2:35][CH2:36][C@@H:37]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1)[OH:38]>>[Cl:45][C:41]1[CH:40]=[C:39]([C@@H:37]([OH:38])[CH2:36][NH:35][CH:29]2[CH2:30][CH2:31][N:26]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][S:16]([C:13]4[CH:14]=[CH:15][C:10]([NH:9][C:8]([NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:33])=[CH:11][CH:12]=4)(=[O:18])=[O:17])=[CH:25][CH:24]=3)[CH2:27][CH2:28]2)[CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 222203144-(3-hexyl-ureido)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamideHCID 56846012(1R)-2-amino-1-(3-chlorophenyl)ethan-1-ol hydrochloride

Product 1

HCID 69655047N-[4-(4-{[(2R)-2-(3-Chlorophenyl)-2-hydroxyethyl]amino}-1-piperidineyl)phenyl]-4-{[(hexylamino)carbonyl]amino}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 (1R)-2-amino-1-(3-chloro-phenyl)-ethanol (which was obtained in Example 1) according to the procedure of Example 278 as a brown solid; 1H NMR (300 MHz, DMSO-d6) δ 0.84 (t, J=6.9 Hz, 3H), 1.20-1.50 (m, 10H), 1.75-1.90 (m, 2H), 2.50-2.80 (m, 5H), 3.00-3.15 (m, 2H), 3.40-3.50 (m, 2H), 4.60 (dd, J=8.1, 3.8 Hz, 1H), 6.29 (t, J=5.7 Hz, 1H), 6.77 (d, J=9.1 Hz, 2H), 6.85 (d, J=9.1 Hz, 2H), 7.25-7.50 (m, 8H), 8.94 (s, 1H), 9.55 (brs, 1H); MS (ES) m/z: 628.1 (MH+); HRMS Calcd. for C32H43ClN5O4S(MH+): 628.2748. Found: 628.2718.

Sources & evidence

ORD record
ord-dd78a26f51fc42f7b3cbc7436831e545
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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