Trifluoroacetic acid → 3-Amino-4-benzyloxy-1-(2-fluorophenyl)pyrazole

HRID 968676Notes

Reaction equation

HRID 968676 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][C:16]1[C:17]([NH:28]C(OC(C)(C)C)=O)=[N:18][N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.CCOC(C)=O>[NH2:28][C:17]1[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[N:18]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 691586054-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

Product 1

HCID 691586673-Amino-4-benzyloxy-1-(2-fluorophenyl)pyrazoleYield 77.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (2 mL) was added to a solution of 4-benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole (1.30 g) in CHCl3 (5 mL) at room temperature and the mixture was stirred for 1.5 hours at room temperature. After being neutralized with 5N NaOH, the mixture was diluted with EtOAc and washed with H2O, sat. NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The semicrystalline residue was triturated with hexane overnight and filtered to yield 742.6 mg of the title compound.

Workup

  1. washwashed with H2O, sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe semicrystalline residue was triturated with hexane overnight
  5. filtrationfiltered

Sources & evidence

ORD record
ord-34e7bbb2286c47f9ae7499e3f4c32fac
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

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