Pyridine → HCID 10518245, compound

HRID 395788Notes

Reaction equation

HRID 395788 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[NH2:18])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>CN(C)C=O>[C:26]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:19])=[C:12]([NH2:18])[CH:13]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10539076HCID 10539076, compound

Product 1

HCID 10518245HCID 10518245, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(4-methoxyphenyl)-2,4-diaminobenzamide (19 g, 73.8 mmol) in N,N-dimethylformamide (250 mL) was added pyridine (6.6 mL, 81 mmol), followed by acetic anhydride (6.6 mL, 70 mmol). After stirring overnight, the solvents were removed in vacuo and the residue was chromatographed over a silica gel (10% tetrahydrofuran/90% chloroform). The appropriate fractions were combined and concentrated in vacuo to give 5.3 g (24%) of the title compound as an off-white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was chromatographed over a silica gel (10% tetrahydrofuran/90% chloroform)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f75fd64f927540159715c440d32d4bfc
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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