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

HRID 130438ノート

反応式

HRID 130438 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]([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]([F: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:33])=[O:34])=[C:28]([F:36])[CH:27]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

生成物 1

HCID 590070834-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-fluorobenzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (1.20 g, 5.09 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-fluorobenzenesulfonyl chloride (2.79 g, 10.2 mmol). The resulting solution was stirred at room temperature overnight, the resin was then filtered off, the solvent evaporated in vacuo and the residue was then passed through an SCX column eluting first with methanol and then by 2M ammonia in methanol. The basic fractions were combined and solvent evaporated in vacuo to afford a crude product which was dry loaded onto a column and purified further by chromatography using a Flashmaster and an elution gradient of 0 to 10% methanol in dichloromethane The relevant fractions were collected, combined and solvent evaporated to afford the title compound (E103). MS (ES+) m/e 472/474 [M+H]+.

後処理

  1. filtrationthe resin was then 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 dry
  7. custompurified further by chromatography
  8. customan elution gradient of 0 to 10% methanol in dichloromethane The relevant fractions were collected
  9. customsolvent evaporated

出典と根拠

ORDレコード
ord-041f5610500f43838fa3704de16aec37
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

反応ノート

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