Pyridine → N4-(tert-butyloxycarbonyl)-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

HRID 1370647Notes

Reaction equation

HRID 1370647 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 110958633-Amino-4-(Boc-amino)pyridine

Product 1

HCID 12069537N4-(tert-butyloxycarbonyl)-N3-(4-methoxybenzoyl)-3,4-pyridinediamineYield 60.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N4-(tert-butyloxycarbonyl)-3,4-pyridinediamine (500 mg, 2.40 mmol) and pyridine (0.213 mL, 2.63 mmol) in methylene chloride (12 mL) was treated with p-anisoyl chloride (408 mg, 2.40 mmol). After 0.75 hr, the mixture was poured into a mixture of ethyl acetate and 1 N aqueous sodium hydroxide. The organic layer was washed with saturated sodium chloride, dried (magnesium sulfate), and filtered. Concentration in vacuo and recrystallization of the residue, followed by flash chromatography (silica gel, hexanes/ethyl acetate) yielded 500 mg (60%) of the title compound.

Workup

  1. washThe organic layer was washed with saturated sodium chloride
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationConcentration
  5. customin vacuo and recrystallization of the residue

Sources & evidence

ORD record
ord-cf69f3cd65ea429590355c4d9c06f89c
Source dataset
uspto-grants-2003_06
Patent number
US06583173B2

Reaction notes

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