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

HRID 130425

Reaktionsgleichung

Reaktionsgleichung von HRID 130425
[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[C:31]([F:32])=[CH:30][C:29]([S:33](Cl)(=[O:35])=[O:34])=[C:28]([F:37])[CH:27]=1>ClCCl>[Br:25][C:26]1[C:31]([F:32])=[CH:30][C:29]([S:33]([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:35])=[C:28]([F:37])[CH:27]=1

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 5745904-Bromo-2,5-difluorobenzenesulfonyl ChlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Produkt 1

HCID 590070874-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2,5-difluorobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (500 mg, 2.12 mmol) in dichloromethane (30 ml) was treated with morpholinomethyl-polystyrene HL resin (1 g, 4 mmol/g loading, 4.24 mmol) followed by 4-bromo-2,5-difluorobenzene sulfonyl chloride (930 mg, 3.2 mmol). The resulting solution was stirred room temperature for 18 hours and was then filtered, washing with dichloromethane, and the filtrate concentrated in vacuo. The residue was then purified using an SCX ion exchange cartridge (Varian bond-elute) eluting with methanol followed by ammonia (0.5M to 2M in methanol). The appropriate fractions were combined and reduced in vacuo to afford a crude product which was purified further by trituration with methanol to afford the desired product D37. MS (ES+) m/e 490/492 [M+H]+.

Aufarbeitung

  1. filtrationwas then filtered
  2. washwashing with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was then purified
  5. washan SCX ion exchange cartridge (Varian bond-elute)
  6. washeluting with methanol
  7. customto afford a crude product which
  8. customwas purified further by trituration with methanol

Quellen und Nachweise

ORD-Eintrag
ord-147463fb8f954a189b7f350b41a72b2c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

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