4-Methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]benzenesulfonamide → N-[4-(4-{[(2R)-2-Hydroxy-2-phenylethyl]amino}-1-piperidineyl)phenyl]-4-methoxybenzenesulfonamide

HRID 1061363Notes

Reaction equation

HRID 1061363 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33](Cl)[CH:32]=1)[OH:30]>>[OH:30][C@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:28][NH:27][CH:22]1[CH2:23][CH2:24][N:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][S:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)(=[O:10])=[O:11])=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 222205564-Methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]benzenesulfonamideHCID 56846012(1R)-2-amino-1-(3-chlorophenyl)ethan-1-ol hydrochloride

Product 1

HCID 69654917N-[4-(4-{[(2R)-2-Hydroxy-2-phenylethyl]amino}-1-piperidineyl)phenyl]-4-methoxybenzenesulfonamide

Procedure

The title compound was prepared from 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol hydrochloride (which was obtained in Example 1) according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.55-1.75 (m, 2H), 2.05-2.15 (m, 2H), 2.50-3.10 (m, 5H), 3.50-3.70 (m, 2H), 3.79 (s, 3H), 4.90-5.05 (m, 1H), 6.10-6.20 (m, 1H), 6.79 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 7.05 (d, J=11.8 Hz, 2H), 7.25-7.50 (m, 5H), 7.60 (d, J=11.8 Hz, 2H), 9.70 (brs, 1H); MS (ES) m/z: 482.2 (MH+); HRMS Calcd. for C26H32N3O4S(MH+): 482.2114. Found: 482.2120.

Sources & evidence

ORD record
ord-f1fdb4bc5fe147f0a7ec0291e0427f06
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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