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

HRID 130424

Reaction equation

HRID 130424 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]([Cl:16])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[Br:17][C:18]1[S:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][CH:19]=1>N1C=CC=CC=1.ClCCl>[Br:17][C:18]1[S:22][C:21]([S:23]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:5][C@H:6]([CH3:8])[NH:7][C@H:2]([CH3:1])[CH2:3]3)[CH:10]=[CH:11][C:12]=2[Cl:16])(=[O:25])=[O:24])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 590070785-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline

Product 1

HCID 590071095-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]-2-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

A solution of 5-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline (D34) (100 mg, 0.42 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with 5-bromo-2-thiophenesulfonyl chloride (132 mg, 0.51 mmol). The solution was stirred at room temperature for 2 hours, quenched with methanol and concentrated in vacuo. The residue was applied to a SCX cartridge (Varian bond-elute, 5 g) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (FlashMaster) (gradient of dichloromethane to 4% metlianol:dichloromethane) to afford the title product (D36). MS (ES+) m/e 464/466/468 [M+H]+.

Workup

  1. customquenched with methanol
  2. concentrationconcentrated in vacuo
  3. washwashed with methanol and 2M ammonia in methanol
  4. concentrationThe combined basic fractions were concentrated in vacuo
  5. customthe resulting residue was purified by column chromatography (FlashMaster) (gradient of dichloromethane to 4% metlianol:dichloromethane)

Sources & evidence

ORD record
ord-b25f89cab3aa45d48fefb505f715d870
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Linked notes

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