Trifluoroacetic acid → HCID 68853778, compound

HRID 2110281Notes

Reaction equation

HRID 2110281 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]([F:23])=[C:21]3[C:17]([C:18]([NH2:24])=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl.C(OCC)(=O)C>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:22]([F:23])=[C:21]3[C:17]([C:18]([NH2:24])=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57636525HCID 57636525, compound

Product 1

HCID 68853778HCID 68853778, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3 g of tert-butyl[4-(3-amino-7-fluoro-1H-indazol-6-yl)phenyl]carbamate in 60 mL of dichloromethane is admixed at ambient temperature with 6 mL of trifluoroacetic acid. The reaction mixture is stirred at ambient temperature for 18 h and concentrated to dryness under reduced pressure. The solid obtained is taken up in ethyl acetate and the solution is treated with 4N aqueous sodium hydroxide solution and then decanted. The organic phase is subsequently washed with distilled water, then with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. The yellow solid obtained (2.08 g) is chromatographed on a silica column (eluent: ethyl acetate). Evaporation to dryness under reduced pressure of the fractions containing the expected product gives 1.88 g of 6-(4-aminophenyl)-7-fluoro-1H-indazol-3-ylamine in the form of a yellow solid, whose characteristics are as follows:

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe solid obtained
  3. customdecanted
  4. washThe organic phase is subsequently washed with distilled water
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe yellow solid obtained (2.08 g)
  9. customis chromatographed on a silica column (eluent: ethyl acetate)
  10. customEvaporation to dryness under reduced pressure of the fractions
  11. additioncontaining the expected product

Sources & evidence

ORD record
ord-53c4143246664251bcc2a578ed8a3091
Source dataset
uspto-grants-2009_04
Patent number
US07517902B2

Reaction notes

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