4-Methylmorpholine → 4-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-methylbenzenesulfonamide

HRID 130437노트

반응식

HRID 130437 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])=[C:28]([CH3:36])[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])=[C:28]([CH3:36])[CH:27]=1

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 27813384-Bromo-2-methylbenzenesulfonyl chlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

생성물 1

HCID 590070954-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-methylbenzenesulfonamide

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 (2.43 g, 4.2 mmol/g loading, 10.2 mmol) followed by 4-bromo-2-methylbenzenesulfonyl chloride (2.75 g, 10.2 mmol). The resulting solution was stirred at room temperature overnight, the resin filtered off, the solvent evaporated in vacuo and the residue passed through an SCX column eluting first with methanol and then 2M ammonia in methanol. The basic fractions were combined and solvent evaporated in vacuo to afford a crude product which was purified further by chromatography on silica gel using a Flashmaster and an elution gradient of 0 to 10% methanol in dichloromethane. The relevant fractions were combined and the solvent evaporated in vacuo to afford the title compound (E102). MS (ES+) m/e 468/470 [M+H]+.

후처리

  1. filtrationthe resin filtered off
  2. customthe solvent evaporated in vacuo
  3. washeluting first with methanol
  4. customsolvent evaporated in vacuo
  5. customto afford a crude product which
  6. customwas purified further by chromatography on silica gel using a Flashmaster
  7. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-ba3a1fc49f3c4486ba5b5d7b5571e318
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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