Trifluoroacetic acid → HCID 178524087, compound

HRID 1256234Notes

Reaction equation

HRID 1256234 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:13]=2[C:12]2[N:22](S(=O)(=O)N(C)C)[N:23]=[CH:24][C:11]=2[N:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:13]=2[C:12]2=[N:22][NH:23][CH:24]=[C:11]2[N:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67494358HCID 67494358, compound

Product 1

HCID 178524087HCID 178524087, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A 250 ml round-bottomed flask is charged with 1.46 g of 5-(2,6-difluorophenyl)-1-(dimethylsulphamoyl)-1H-pyrazolo[4,3-c]isoquinoline-7-carboxylic acid in 100 ml of DCM and then 20 ml of TFA are added. The mixture is stirred at RT for 16 h. It is concentrated under RP and the solid obtained is taken up in 30 ml of saturated aqueous NaHCO3 solution and extracted with three times 30 ml of AcOEt. The aqueous phase is acidified to a pH of 1 by addition of 37% HCl and extracted with AcOEt. The organic phase is washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated under RP to give 927 mg of 5-(2,6-difluorophenyl)-2H-pyrazolo[4,3-c]isoquinoline-7-carboxylic acid (beige solid), LC-MS-DAD-ELSD: 326(+)=(M+H)(+).

Workup

  1. concentrationIt is concentrated under RP
  2. customthe solid obtained
  3. extractionextracted with three times 30 ml of AcOEt
  4. additionThe aqueous phase is acidified to a pH of 1 by addition of 37% HCl
  5. extractionextracted with AcOEt
  6. washThe organic phase is washed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under RP

Sources & evidence

ORD record
ord-9fc60dcee1034aed8c5e5cc9d0f109f3
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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