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

HRID 130441

반응식

HRID 130441 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]([O:16][CH3:17])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.CN1CCOCC1.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:16][CH3:17])(=[O:34])=[O:33])=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

생성물 1

HCID 444527764-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (1.20 g, 5.1 mmol) in dichloromethane (35 ml) was treated with morpholinomethyl-polystyrene HL resin (2.45 g, 4.2 mmol/g loading, 10.29 mmol) followed by 4-bromobenzenesulfonyl chloride (2.60 g, 10.2 mmol). The resulting solution was stirred at room temperature overnight (˜24hours)and then the resin filtered off with methanol and the solvent evaporated in vacuo. The residue was passed through an SCX column eluting first with methanol followed by 2M ammonia in methanol. The relevant fractions were collected, combined and the solvent evaporated in vacuo. The crude product was purified by Flashmaster causing an elution gradient of 0 to 10% methanol in dichloromethane. The relevant fractions were collected, combined and the solvent evaporated to afford the title compound (E106). MS (ES+) m/e 454/456 [M+H]+.

후처리

  1. filtrationthe resin filtered off with methanol
  2. customthe solvent evaporated in vacuo
  3. washeluting first with methanol
  4. customThe relevant fractions were collected
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by Flashmaster
  7. customThe relevant fractions were collected
  8. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-5f4f9e09ca37412db2a3eae206990843
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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