Pyridine → HCID 178426560, compound

HRID 564017Notes

Reaction equation

HRID 564017 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]2[N:18]=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)=[O:8].N1C=CC=CC=1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]2[N:18]=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)=[O:8])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178426380HCID 178426380, compound

Product 1

HCID 178426560HCID 178426560, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of 5-Amino-N-(3H-imidazo[4,5-b]pyridin-6-yl)-2-methyl-benzamide (from example k) were dissolved in 0.5 ml dry DMF and 0.5 ml pyridine and treated dropwise at room temperature with 66 mg benzoyl chloride. After 16 hrs the solvents were removed under vacuum and the residue was stirred for 1 hr at room temperature in a mixture of 2 ml methanol and 1 ml concentrated ammonia. Solvents were removed under vacuum and the residue was purified by HPLC/MS in methanol/water/acetic acid. Product containing fractions were pooled and concentrated under vacuum. Precipitated product was collected by filtration and washed with dilute ammonia to yield 11 mg of the title product.

Workup

  1. customAfter 16 hrs the solvents were removed under vacuum
  2. customSolvents were removed under vacuum
  3. customthe residue was purified by HPLC/MS in methanol/water/acetic acid
  4. additionProduct containing fractions
  5. concentrationconcentrated under vacuum
  6. filtrationPrecipitated product was collected by filtration
  7. washwashed with dilute ammonia

Sources & evidence

ORD record
ord-9dbc64cc028a498380bd6638ff97eedc
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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