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

HRID 43376Notes

Reaction equation

HRID 43376 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.CO>[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

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 591613281,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 591613863-methyl-4-{[(3R)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate (may be prepared as described in Description 19) (3.24 g, 8.54 mmol) and TFA (7.00 ml, 91.0 mmol) in dry DCM (10 ml) was stirred at rt for 1 h, then concentrated under vacuum, azetroping with toluene (25 ml) to give an orange oil. This was redissolved in MeOH (10 ml) then applied to an SCX-2 cartridge (50 g), washing with MeOH. The product was eluted with 2M NH3 in MeOH; concentration under vacuum gave the title compound as a pale orange oil (8.17 mmol).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give an orange oil
  3. washwashing with MeOH
  4. washThe product was eluted with 2M NH3 in MeOH
  5. concentrationconcentration under vacuum

Sources & evidence

ORD record
ord-8157cc6e5a8a49629901a9b2620fa4c1
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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