Trifluoroacetic acid → HCID 10451352, compound

HRID 1437288Notes

Reaction equation

HRID 1437288 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]([C:34]3[CH:35]=[N:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=3)[N:24]=2)=[O:22])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:41][O:40][C:37]1[N:36]=[CH:35][C:34]([N:25]2[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:27][C:23]([C:21]([N:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[O:22])=[N:24]2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57940651HCID 57940651, compound

Product 1

HCID 10451352HCID 10451352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, trifluoroacetic acid (2.4 mL) was added to a solution of the above-mentioned 1-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]piperazine-4-carboxylic acid tert-butyl ester (0.639 g) in methylene chloride (15 mL), followed by stirring of the mixture for 0.7 hours. The reaction solvent was removed under reduced pressure, and the residue was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate. The aqueous layer was extracted with chloroform. The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an oily product (0.446 g, 89%).

Workup

  1. customThe reaction solvent was removed under reduced pressure
  2. customthe residue was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate
  3. extractionThe aqueous layer was extracted with chloroform
  4. washwashed with saturated brine
  5. dry with materialby drying over sodium sulfate anhydrate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-f2c491db6333426080d2aaf346a6ab05
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

Loading…