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

HRID 130456Notes

Reaction equation

HRID 130456 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[S:30][C:29]([S:31](Cl)(=[O:33])=[O:32])=[CH:28][CH:27]=1>ClCCl>[Br:25][C:26]1[S:30][C:29]([S:31]([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:32])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 590070585-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (1.00 g, 4.25 mmol) in dichloromethane (50 ml) was treated with morpholinomethyl-polystyrene HL resin (2.10 g, 4.0 mmol/g loading, 8.50 mmol) followed by 5-bromo-2-thiophenesulfonyl chloride (1.33 g, 5.09 mmol). The resulting solution was stirred at room temperature overnight and was then filtered and the solvent evaporated. The residue was then chromatographed over silica gel (Flashmaster (II)) eluting with 0 to 10% methanol in dichloromethane 90% for 5 mins, 0-10% 20 mins and 10% 10 mins). The compound was then purified by mass directed autoprep HPLC and the residue further purified by SCX, eluting with methanol first and then NH4OH/methanol. (E122). MS (ES+) m/e 460/462 [M+H]+.

Workup

  1. filtrationwas then filtered
  2. customthe solvent evaporated
  3. customThe residue was then chromatographed over silica gel (Flashmaster (II))
  4. washeluting with 0 to 10% methanol in dichloromethane 90% for 5 mins
  5. custom0-10% 20 mins and 10% 10 mins
  6. customThe compound was then purified by mass
  7. customthe residue further purified by SCX
  8. washeluting with methanol first

Sources & evidence

ORD record
ord-0e936dc99a2249608c026d0eeb3c96bc
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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