Pyridine → HCID 12069542, compound

HRID 1355623Notes

Reaction equation

HRID 1355623 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[NH2:18])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:27](Cl)(=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[NH:18][C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 53958127HCID 53958127, compound

Product 1

HCID 12069542HCID 12069542, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N3-(4-tert-butylbenzoyl)-3,4-pyridinediamine (400 mg, 1.49 mmol), pyridine (0.264 mL), and p-anisoyl chloride (0.254 mL, 1.49 mmol) in toluene (12 mL) was heated at reflux for 3 h. The mixture was filtered and the filtrate poured into a mixture of ethyl acetate and water. The organic layer was washed three times with water, once with saturated sodium chloride solution, dried, and filtered. Concentration in vacuo and purification of the residue by recrystallization (methanol/ethyl acetate/hexanes) followed by flash chromatography (silica gel, ethyl acetate/methylene chloride) yielded 75 mg (13%) of the title compound.

Workup

  1. temperatureat reflux for 3 h
  2. filtrationThe mixture was filtered
  3. additionthe filtrate poured into a mixture of ethyl acetate and water
  4. washThe organic layer was washed three times with water
  5. dry with materialonce with saturated sodium chloride solution, dried
  6. filtrationfiltered
  7. concentrationConcentration
  8. customin vacuo and purification of the residue
  9. customby recrystallization (methanol/ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2523ad5f0791498582b2d4b200409f23
Source dataset
uspto-grants-2003_07
Patent number
US06586459B2

Reaction notes

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