4-Methylmorpholine → HCID 59007060, compound

HRID 130440Notes

Reaction equation

HRID 130440 reaction equation
[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][C:27]=1[F:36]>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][C:27]=1[F:36]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27782184-Bromo-3-fluorobenzenesulfonyl chlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 59007060HCID 59007060, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (400 mg,1.70 mmol) in dichloromethane (15 ml) was treated with morpholinomethyl-polystyrene HL resin (1.00 g, 3.4 mmol/g loading) followed by 4-bromo-3-fluorobenzenesulfonyl chloride (0.50 ml, 930 mg, 3.40 mmol). The resulting solution was stirred at room temperature for overnight (20 hours). The reaction mixture and was then filtered, washed with methanol, and the solvent evaporated in vacuo. The residue was applied to an SCX column eluting first with methanol and then 2M ammonia in methanol. The fractions containing product were collected, combined and evaporated in vacuo to afford a crude product which was dry loaded onto a column and purified further by chromatography using a Flashmaster with an eluting gradient of 0 to 5% methanol in dichloromethane over 40 mins. Fractions containing product were combined and evaporated in vacuo to afford the title compound (E105). MS (ES+) m/e 472/474 [M+H]+.

Workup

  1. filtrationThe reaction mixture and was then filtered
  2. washwashed with methanol
  3. customthe solvent evaporated in vacuo
  4. washeluting first with methanol
  5. additionThe fractions containing product
  6. customwere collected
  7. customevaporated in vacuo
  8. customto afford a crude product which
  9. customwas dry
  10. custompurified further by chromatography
  11. customover 40 mins
  12. additionFractions containing product
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-c149539ef38c44f3baed76d32096c164
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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