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

HRID 43371Notes

Reaction equation

HRID 43371 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 10) (2.88 g, 7.59 mmol) and TFA (10 ml, 130 mmol) in dry DCM (10 ml) was stirred at room temperature for 1 hour, then concentrated in vacuo, azeotroping with toluene (25 ml) to give a brown oil. This was partitioned between DCM (50 ml) and saturated aqueous NaHCO3 (50 ml), then the aqueous layer was 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. customazeotroping with toluene (25 ml)
  3. customto give a brown oil
  4. customThis was partitioned between DCM (50 ml) and saturated aqueous NaHCO3 (50 ml)
  5. extractionthe aqueous layer was extracted with DCM (50 ml)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c648c13f068646c8b0474e016e9d4608
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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