4-(Chlorosulfonyl)benzoic acid → 4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-benzoic acid

HRID 1061349Notes

Reaction equation

HRID 1061349 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>>[O:28]=[C:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][S:2]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)(=[O:4])=[O:3])=[CH:17][CH:18]=2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 222202954-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-benzoic acid

Procedure

The title compound was prepared from 4-(chlorosulfonyl)benzoic acid and 1-(4-amino-phenyl)-piperidine-4-one hydrochloride (which was obtained in Example 224) according to the procedure B of Example 225 as a pale grey solid; 1H NMR (300 MHz, DMSO-d6) δ 2.36 (t, J=6.0 Hz, 4H), 3.49 (t, J=6.0 Hz, 4H), 6.87 (d, J=9.3 Hz, 2H), 6.91 (d, J=9.3 Hz, 2H), 7.77 (d, J=8.1 Hz, 2H), 8.04 (d, J=8.1 Hz, 2H), 9.97 (s, 1H), 13.10 (brs, 1H); MS (ES) m/z: 374.9 (MH+); HRMS Calcd. for C18H19N2O5S(MH+): 375.1009. Found: 375.1009.

Sources & evidence

ORD record
ord-b0c3181183c74090a94f5c2cc716cdf6
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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