4-Toluenesulfonyl chloride → 4-Methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide

HRID 230486Notes

Reaction equation

HRID 230486 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23].[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>>[CH3:41][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)=[CH:4][C:3]=2[NH:21][S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:23])=[O:24])(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22272479N-(2-amino-5-(4-boc-1-piperazinyl)-phenyl)-benzenesulfonamide

Product 1

HCID 102280314-Methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide

Procedure

4-Methyl-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]benzenesulfonamide was synthesized from N-{2-amino-5-(4-t-butyloxycarbonyl-piperazinyl)-phenyl}benzenesulfonamide and p-toluenesulfonylchloride (46 mg, 0.239 mmol) according to general method 3 to give 70 mg of a purple solid. MS (posES-FIA) m/z=Found: 487.2; Calcd: 487.14; 1H-NMR δ 7.73-7.45 (m, 7H), 7.26 (d, 2H), 6.74 (s, 1H), 6.62-6.60 (m, 2H), 3.69 (app t, 2H), 3.39 (app t, 2H), 3.29-3.74 (m, 4H), 2.38 (s, 3H).

Sources & evidence

ORD record
ord-d8a03d38c48f4d858887d8b7330f08cd
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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