Trifluoroacetic acid → HCID 59516117, compound

HRID 1799408Notes

Reaction equation

HRID 1799408 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=2)[C:19]=1[S:20][CH2:21][CH2:22][CH3:23])=[O:14])(C)(C)C>C(Cl)Cl>[CH3:34][O:33][C:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:18]2[C:19]([S:20][CH2:21][CH2:22][CH3:23])=[C:15]([C:13]([OH:14])=[O:12])[CH:16]=[N:17]2)=[CH:26][CH:27]=1)=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59516113HCID 59516113, compound2×

Product 1

HCID 59516117HCID 59516117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.5 ml) was added to a stirred solution of 1-(4-Methoxycarbonyl-benzyl)-5-propylsulfanyl-1H-pyrazole-4-carboxylic acid tert-butyl ester (Intermediate #46) (274 mg, 0.70 mmol) in DCM (6 ml). The reaction was stirred at ambient temperature for 3 hours then evaporated in vacuo. The resulting gum was sonicated with isohexane to yield a solid. The solvent was removed then the white solid was dissolved in EtOAc and evaporated in vacuo to yield the title compound as an off white solid (236 mg, 100%).

Workup

  1. customthen evaporated in vacuo
  2. customThe resulting gum was sonicated with isohexane
  3. customto yield a solid
  4. customThe solvent was removed
  5. dissolutionthe white solid was dissolved in EtOAc
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-343c9556b1734ae282c0c4333d9932c3
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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