Trifluoroacetic acid → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-(2,2,2-trifluoroethoxy)-4-pyrimidinyl]-1-piperazinesulfonamide

HRID 2388750Notes

Reaction equation

HRID 2388750 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([NH:17][C:18]2[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[N:21]=[C:20]([S:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=3[F:39])[N:19]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:39][C:33]1[C:34]([F:38])=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][S:30][C:20]1[N:19]=[C:18]([NH:17][S:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)(=[O:15])=[O:16])[CH:23]=[C:22]([O:24][CH2:25][C:26]([F:29])([F:27])[F:28])[N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53628348HCID 53628348, compound

Product 1

HCID 59558755N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-(2,2,2-trifluoroethoxy)-4-pyrimidinyl]-1-piperazinesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[[[2-[[(2,3-difluorophenyl)methyl]thio]-6-(2,2,2-trifluoroethoxy)-4-pyrimidinyl]amino]sulfonyl]-1-piperazinecarboxylic acid-1,1-dimethylethyl ester (the product from step i) (0.21 g) in DCM (2 mL) was added trifluoroacetic acid (2 mL) and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was evaporated, the residue was azeotroped with Et2O (×2) and then purified by reverse phase HPLC eluting with acetonitrile/aq. 0.2% trifluoroacetic acid mixtures to give title compound as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was azeotroped with Et2O (×2)
  3. custompurified by reverse phase HPLC
  4. washeluting with acetonitrile/aq

Sources & evidence

ORD record
ord-6e32cbc58e234beba796f22659ea3e8d
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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