Ammonium formate → HCID 90052088, compound

HRID 2284667Notes

Reaction equation

HRID 2284667 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]([F:28])([F:27])[CH:7]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]>CO.[C].[Pd]>[NH2:24][C:20]1[CH:19]=[C:18]([NH:17][CH:7]([C:6]([F:5])([F:27])[F:28])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90052061HCID 90052061, compound

Product 1

HCID 90052088HCID 90052088, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To 10% palladium-carbon (50 mg) and ammonium formate (135 mg), a solution of tert-butyl (3,3,3-trifluoro-2-((3-nitrophenyl)amino)propyl)carbamate (C17, 100 mg) in methanol (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. The insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate and water were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain tert-butyl (2-((3-aminophenyl)amino)-3,3,3-trifluoropropyl)carbamate (C18, 45 mg).

Workup

  1. customThe insoluble matter was removed by filtration through Cerite
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo the obtained residue, ethyl acetate and water were added
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4922f7a1a94d41d68d6879d0bd8c48f7
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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