Trifluoroacetic acid → HCID 58628306, compound

HRID 1443850Notes

Reaction equation

HRID 1443850 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH:21][C:22]([C:24]2[CH:25]=[N:26][C:27]3[N:28]([N:30]=[CH:31][C:32]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[CH:29]=2)=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH:21][C:22]([C:24]2[CH:25]=[N:26][C:27]3[N:28]([N:30]=[CH:31][C:32]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[CH:29]=2)=[O:23])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 58628271HCID 58628271, compound

Product 1

HCID 58628306HCID 58628306, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-{2-(4-t-butoxycarbonyl piperazino)phenyl}methyl 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-6-amide (300 mg) and trifluoroacetic acid (0.42 ml) in chloroform (6 ml) was heated at reflux over 6 hours. The reactant was cooled, and ice and a 2N aqueous sodium hydroxide solution (3 ml) were added, and thereafter extracted with chloroform. The organic layer was dried with magnesium sulfate, and thereafter the solvent was distilled under a reduced pressure. The residue was purified by an alumina column chromatography, and thereafter recrystallized from tetrahydrofuran-diisopropyl ether to yield N-(2-piperazinophenyl)methyl 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-6-amide (220 mg, 90%). mp: 185-188° C.

Workup

  1. temperatureat reflux over 6 hours
  2. temperatureThe reactant was cooled
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. distillationthe solvent was distilled under a reduced pressure
  6. customThe residue was purified by an alumina column chromatography
  7. customrecrystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-563130bae083426d9fb2c8b8b97099d4
Source dataset
uspto-grants-2010_02
Patent number
US07662826B2

Reaction notes

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