5-Bromothiophene-2-sulfonyl chloride → 5-Bromo-N-{5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]phenyl]-2-thiophenesulfonamide

HRID 130430Notes

Reaction equation

HRID 130430 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[Br:24][C:25]1[S:29][C:28]([S:30](Cl)(=[O:32])=[O:31])=[CH:27][CH:26]=1>ClCCl.N1C=CC=CC=1>[Br:24][C:25]1[S:29][C:28]([S:30]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:32])=[O:31])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 590070925-(cis-3,5-Dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]aniline

Product 1

HCID 590070965-Bromo-N-{5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]phenyl]-2-thiophenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]aniline (D39) (300 mg, 0.96 mmol) in dichloromethane (5 ml) and pyridine (5 ml) was added 5-bromo-2-thiophenesulfonyl chloride (505 mg, 1.93 mmol) and the mixture stirred at room temperature for 4 hours. The mixture was then reduced in vacuo and the residue purified by SCX (eluting with methanol then ammonia 2M in methanol). The appropriate fractions were combined and reduced and the residue purified by trituaration with methanol to afford the title compound (D42). MS (ES+) m/e 536/538 [M+H]+.

Workup

  1. customthe residue purified by SCX (
  2. washeluting with methanol
  3. customthe residue purified by trituaration with methanol

Sources & evidence

ORD record
ord-4ecedd6316164cc78f6a55d979f81622
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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