4-(Thiophen-2-yl)benzene-1-sulfonyl chloride → N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

HRID 130434

반응식

HRID 130434 반응식
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[NH2:12])[CH2:3]1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.ClCCl.ClCCl>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([NH:12][S:29]([C:26]3[CH:25]=[CH:24][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[CH:28][CH:27]=3)(=[O:30])=[O:31])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:3]1

참가 물질

5

반응물 2

HCID 183877594-(Thiophen-2-yl)benzene-1-sulfonyl chlorideHCID 590070453-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

생성물 1

HCID 11518200N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21875418Pyridine methylene chloride용매

실험 절차

A solution of 3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (117 mg, 0.5 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with a solution 4-(2-thienyl)benzenesulfonyl chloride (WO 9827069) (143 mg, 0.55 mmol) in dichloromethane (2 ml). The solution was stirred at room temperature for 24 hours, quenched with methanol (2 ml) and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water (×3). The organic phase 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 (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane) to afford the title product (E11). MS (ES+) m/e 458 [M+H]+.

후처리

  1. customquenched with methanol (2 ml)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water (×3)
  5. washwashed with methanol and 2M ammonia in methanol
  6. concentrationThe combined basic fractions were concentrated in vacuo
  7. customthe resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane)

출처 및 근거

ORD 기록
ord-c605a5a7a06b49218e76290c326b7258
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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