Diisopropylethylamine → (2S)-4-({4-[(Difluoromethyl)oxy]phenyl}sulfonyl)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazine

HRID 43408Notes

Reaction equation

HRID 43408 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=1)=[O:9].[F:17][CH:18]([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:30][CH:18]([F:17])[O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([N:6]2[CH2:5][CH2:4][N:3]([C:8]([C:10]3[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[O:9])[C@@H:2]([CH3:1])[CH2:7]2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27782234-(Difluoromethoxy)benzenesulfonyl chlorideHCID 59161378(2S)-2-Methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazine

Product 1

HCID 59161383(2S)-4-({4-[(Difluoromethyl)oxy]phenyl}sulfonyl)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazineYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazine (Description 13) (100 mg, 0.456 mmol) in DMF (10 ml) was added 4-[(difluoromethyl)oxy]benzenesulfonyl chloride (133 mg, 0.547 mmol). Finally DIPEA (0.239 ml, 1.368 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 washed 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 (72 mg) as a white powder.

Workup

  1. customSolvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution washed 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-c6dc240b9afc405b872d332be0c3b04c
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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