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

HRID 130424

反応式

HRID 130424 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21875418Pyridine methylene chloride溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-b25f89cab3aa45d48fefb505f715d870
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

関連ノート

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