Dichloromethane → HCID 23090364, compound

HRID 1437297Notes

Reaction equation

HRID 1437297 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([C:27]3[CH:28]=[N:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)[Cl:36]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[ClH:36].[CH3:34][O:33][C:30]1[N:29]=[CH:28][C:27]([N:18]2[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:20][C:16]([C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:15])=[N:17]2)=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 57940651HCID 57940651, compound

Product 1

HCID 23090364HCID 23090364, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 4-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (332 mg) obtained in Example 64 in methylene chloride (2 mL), anisole (0.4 mL) and trifluoroacetic acid (1.6 mL) were added, and the mixture was stirred at room temperature for 30 minutes. The reaction solvent was removed under reduced pressure, and the residue was partitioned between water and diethyl ether. The aqueous layer was alkalinized with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate four times. The organic layers were combined, followed by drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was dissolved in a solvent mixture of diethyl ether and a small amount of methanol. 1M HCl-ethanol (0.78 mL) was added thereto, and the precipitated crystals were collected through filtration. The thus-obtained matter was recrystallized from methanol-diethyl ether, to thereby give the title compound (229 mg, 76%).

Workup

  1. customThe reaction solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and diethyl ether
  3. extractionextracted with ethyl acetate four times
  4. dry with materialby drying over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in a solvent mixture of diethyl ether
  8. addition1M HCl-ethanol (0.78 mL) was added
  9. filtrationthe precipitated crystals were collected through filtration
  10. customThe thus-obtained matter was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-1411c9645aef4fd58273193475174982
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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