Trifluoroacetic acid → 3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

HRID 418277Notes

Reaction equation

HRID 418277 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[C@@H:14]([CH3:25])[CH2:13]2)(=[O:11])=[O:10])=[C:5]([CH3:26])[CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:25])[CH2:13]1)(=[O:11])=[O:10])[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591520981,1-dimethylethyl(2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 591520673-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl(2S)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate (may be prepared as described in Description 8) (2.88 g, 7.59 mmol) and TFA (10 ml, 130 mmol) in dry DCM (10 ml) was stirred at rt for 1 hour, then concentrated in vacuo, azetroping with toluene (25 ml) to give a brown oil. This was partitioned between DCM (50 ml) and sat. aq. NaHCO3 (50 ml), then the aq. layer extracted with DCM (50 ml). The combined organic layers were passed through a hydrophobic frit and concentrated in vacuo to give the title compound as a yellow oil (2.29 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a brown oil
  3. customThis was partitioned between DCM (50 ml) and sat. aq. NaHCO3 (50 ml)
  4. extractionthe aq. layer extracted with DCM (50 ml)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4ea9c346d984d9a9958828c2f45b9b7
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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