N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide → N-(4-{4-[4-((2R)-2-Hydroxy-2-phenyl-ethylamino)-piperidin-1-yl]-phenylsulfamoyl}-phenyl)-acetamide

HRID 1061360Notes

Reaction equation

HRID 1061360 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[NH2:29][CH2:30][C@@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35](Cl)[CH:34]=1)[OH:32]>>[OH:32][C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][NH:29][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamideHCID 56846012(1R)-2-amino-1-(3-chlorophenyl)ethan-1-ol hydrochloride

Product 1

HCID 69654893N-(4-{4-[4-((2R)-2-Hydroxy-2-phenyl-ethylamino)-piperidin-1-yl]-phenylsulfamoyl}-phenyl)-acetamide

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol (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), 2.06 (s, 3H), 2.00-2.15 (m, 2H), 2.50-3.20 (m, 5H), 3.55-3.70 (m, 2H), 4.90-5.00 (m, 1H), 6.00-6.20 (brs, 1H), 6.80 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 7.25-7.52 (m, 5H), 7.59 (d, J=8.7 Hz, 2H), 7.70 (d, J=8.7 Hz, 2H), 10.41 (s, 1H); MS (ES) m/z: 509.2 (MH+); HRMS Calcd. for C27H33N4O4S(MH+): 509.2223. Found: 509.2194.

Sources & evidence

ORD record
ord-1b9c3bf071bd4fe182d439b2c6c1d789
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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