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

HRID 130424

반응식

HRID 130424 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[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21875418Pyridine methylene chloride용매

실험 절차

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]+.

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) (gradient of dichloromethane to 4% metlianol:dichloromethane)

출처 및 근거

ORD 기록
ord-b25f89cab3aa45d48fefb505f715d870
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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