Trifluoroacetic acid → HCID 57940616, compound

HRID 1437293Notes

Reaction equation

HRID 1437293 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[C:32]([O:34][CH2:35][CH3:36])[CH:31]=[CH:30][N:29]=3)[N:25]([C:37]3[CH:38]=[N:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)[N:24]=2)=[O:22])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:35]([O:34][C:32]1[CH:31]=[CH:30][N:29]=[C:28]([C:26]2[N:25]([C:37]3[CH:38]=[N:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)[N:24]=[C:23]([C:21]([N:18]3[CH2:19][CH2:20][N:15]([CH3:13])[CH2:16][CH2:17]3)=[O:22])[CH:27]=2)[CH:33]=1)[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68438105HCID 68438105, compound

Product 1

HCID 57940616HCID 57940616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, trifluoroacetic acid (1.4 mL) was added to a solution of the above-obtained 4-[5-(4-ethoxy-2-pyridyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (0.135 g) in methylene chloride (2.7 mL), and the mixture was stirred for 30 minutes. The solvent was removed under reduced pressure, and the residue was dissolved in ethanol (2.7 mL). To the mixture were added 35% aqueous formalin solution (0.114 g), acetic acid (0.076 mL) and sodium cyanoborohydride (50.0 mg). The resultant mixture was stirred for 100 minutes at room temperature. Sodium cyanoborohydride (33.3 mg) was further added thereto, and the mixture was stirred for 50 minutes. The reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol). Subsequently, the residue was purified through silica gel thin-layer chromatography (chloroform-methanol), to thereby give the title compound as an oily product (86.9 mg, 78%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (2.7 mL)
  3. additionTo the mixture were added 35% aqueous formalin solution (0.114 g), acetic acid (0.076 mL) and sodium cyanoborohydride (50.0 mg)
  4. stirringThe resultant mixture was stirred for 100 minutes at room temperature
  5. additionSodium cyanoborohydride (33.3 mg) was further added
  6. stirringthe mixture was stirred for 50 minutes
  7. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and chloroform
  8. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  9. filtrationAfter filtration
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (chloroform-methanol)
  12. customSubsequently, the residue was purified through silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6098235ed13648b59877d0bce2d0876f
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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