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

HRID 428014Notes

Reaction equation

HRID 428014 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-55d79a7d0d1f4315b834823f5bdcec84
Source dataset
uspto-grants-2001_11
Patent number
US06313151B1

Reaction notes

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