p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]benzenesulfonamide

HRID 130423

반응식

HRID 130423 반응식
[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[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([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:26])=[O:25])=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 590070785-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline

생성물 1

HCID 590070904-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]benzenesulfonamide

시약·촉매·용매 1

HCID 21875418Pyridine methylene chloride용매

실험 절차

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-chloroaniline (D34) (108 mg, 0.45 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with 4-bromobenzenesulfonyl chloride (138 mg, 0.54 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) (dichloromethane to 5% methanol:dichloromethane) to afford some pure product. The impure fractions were purified further by MDAP, and combined with the above pure product to afford the title product (D35). MS (ES+) m/e 458/460/462 [M+H]+.

후처리

  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) (dichloromethane to 5% methanol:dichloromethane)
  6. customto afford some pure product
  7. customThe impure fractions were purified further by MDAP

출처 및 근거

ORD 기록
ord-f07f4d9910774fc9810990896b77eba6
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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