Diisopropylethylamine → 1-[(6-Methyl-3-pyridinyl)carbonyl]-4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine

HRID 43409Notes

Reaction equation

HRID 43409 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]([F:30])([F:29])[O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:29])[F:30])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 167870611-[(6-Methylpyridin-3-YL)carbonyl]piperazine

Product 1

HCID 302859691-[(6-Methyl-3-pyridinyl)carbonyl]-4-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazineYield 20.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[(6-methyl-3-pyridinyl)carbonyl]piperazine (may be prepared as described in Description 14) (100 mg, 0.487 mmol) in DMF (10 ml) was added 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (152 mg, 0.585 mmol). Finally DIPEA (0.255 ml, 1.462 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. Solvent was removed by evaporation, the residue was dissolved in ethyl acetate and the solution extracted with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and evaporated to dryness and the residue was purified by MDAP to yield the title compound (42 mg) as a white powder.

Workup

  1. customSolvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionthe solution extracted with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe residue was purified by MDAP

Sources & evidence

ORD record
ord-51c133a4797542e6a0a82ff1f95be02d
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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