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

HRID 1061390Notes

Reaction equation

HRID 1061390 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:28][CH2:29][C@H:30]([OH:45])[CH2:31][O:32][C:33]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]2[C:34]=1[CH2:35][CH2:36][C:37](=[O:44])[NH:38]2>>[OH:45][C@H:30]([CH2:31][O:32][C:33]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]2[C:34]=1[CH2:35][CH2:36][C:37](=[O:44])[NH:38]2)[CH2:29][NH:28][CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][S:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)(=[O:12])=[O:13])=[CH:20][CH:19]=2)[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 222204173,4-Dimethoxy-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 69654735N-{4-[4-({(2S)-2-Hydroxy-3-[(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-5-quinolinyl)oxy]-propyl}amino)-1-piperidineyl]phenyl}-3,4-dimethoxybenzenesulfonamide

Procedure

The title compound was prepared from 3,4-dimethoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 242) 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 1.20-1.40 (m, 2H), 1.80-1.95 (m, 2H), 2.39 (t, J=7.2 Hz, 2H), 2.50-2.75 (m, 5H), 2.82 (t, J=7.2 Hz, 2H), 3.45-3.55 (m, 2H), 3.63 (s, 3H), 3.72 (s, 3H), 3.70-3.85 (m, 3H), 4.91 (brs, 1H), 6.44 (d, J=8.8 Hz, 1H), 6.60 (d, J=8.8 Hz, 1H), 6.78 (d, J=9.1 Hz, 1H), 6.88 (d, J=9.1 Hz, 1H), 7.02 (d, J=8.5 Hz, 1H), 7.18 (dd, J=8.5, 2.1 Hz, 1H), 7.36 (d, J=2.1 Hz, 1H),8.72 (s, 1H), 9.17 (brs, 1H); MS (ES) m/z: 627.1 (MH+); HRMS Calcd. for C31H39N4O8S(MH+): 627.2489. Found: 627.2458.

Sources & evidence

ORD record
ord-3097736b7db44d3793d66e5ee4bcb61c
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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