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

HRID 43386Notes

Reaction equation

HRID 43386 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].[Br:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:17][C:18]1[CH:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:21]=[CH:20][C:19]=1[S:28]([N:6]1[CH2:5][CH2:4][N:3]([C:8]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[O:9])[C@@H:2]([CH3:1])[CH2:7]1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27786112-Bromo-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 59161378(2S)-2-Methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazine

Product 1

HCID 59161388(2S)-4-{[2-bromo-4-(trifluoromethyl)phenyl]sulfonyl}-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazineYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-methyl-1-[(6-methyl-3-pyridinyl)carbonyl]piperazine (may be prepared as described in Description 13) (200 mg, 0.912 mmol) in DCM (10 mL) was added 2-bromo-4-(trifluoromethyl)benzenesulfonyl chloride (295 mg, 0.912 mmol) followed by DIPEA (0.159 mL, 0.912 mmol). The reaction mixture was left stirring at room temperature for 15 h. The solvent was removed by evaporation and the crude residue was dissolved in DCM (30 ml), washed with saturated sodium bicarbonate (40 ml), dried (hydrophobic frit) and evaporated under vacuum. The crude product was purified by silica chromatography using a gradient EtOAc/iso-hexane from 20/80 to 100/0. The desired fractions were combined and concentrated under vacuum to give the title compound (216 mg).

Workup

  1. waitThe reaction mixture was left
  2. customThe solvent was removed by evaporation
  3. dissolutionthe crude residue was dissolved in DCM (30 ml)
  4. washwashed with saturated sodium bicarbonate (40 ml)
  5. customdried (hydrophobic frit)
  6. customevaporated under vacuum
  7. customThe crude product was purified by silica chromatography
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-268b1917a9fa4ff28bdd9e1cfbb036f2
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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