Trifluoroacetic acid → N3-(4-methoxybenzoyl)-3,4-pyridinediamine

HRID 1370648Notes

Reaction equation

HRID 1370648 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([NH:15][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[NH2:8])=[O:25])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12069537N4-(tert-butyloxycarbonyl)-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

Product 1

HCID 12069538N3-(4-methoxybenzoyl)-3,4-pyridinediamineYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N4-(tert-butyloxycarbonyl)-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (600 mg, 1.75 mmol) in methylene chloride (8 mL) was treated with trifluoroacetic acid (1.35 mL, 17.5 mmol). After 6.5 h, the mixture was concentrated and the residue dissolved in water and treated with 5 N aqueous sodium hydroxide. The resulting precipitate was collected by filtration yielding 325 mg (76%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue dissolved in water
  3. additiontreated with 5 N aqueous sodium hydroxide
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0cb08127ab5045cca514febf35ed74e0
Source dataset
uspto-grants-2003_06
Patent number
US06583173B2

Reaction notes

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