Pyridine → HCID 20251889, compound

HRID 1284484Notes

Reaction equation

HRID 1284484 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:15]1([CH2:20][C:21](O)=[O:22])[CH:19]=[CH:18][N:17]=[CH:16]1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[N:15]1([CH2:20][C:21]([NH:1][C:2]2[C:3]([NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:22])[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 656129Imidazole-1-acetic acidHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 20251889HCID 20251889, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3-amino-2-anilinopyridine (0.5 g), 2-(imidazol-1-yl)acetic acid (0.38 g) and pyridine (0.24 ml) in chloroform (5 ml) was dropwise added phosphorus oxychloride (0.28 ml) and the mixture was refluxed for 1.5 hours. After being cooled, the reaction mixture was decanted and the residue was poured into saturated aqueous sodium bicarbonate. The mixture was extracted three times with ethyl acetate. The combined extract was dried over magnesiumsulfate and the solvent was evaporated under reduced pressure. The resultant residue was triturated in ethyl acetate (10 ml) to give 2-(imidazol-1-yl)-N-(2-anilinopyridin 3-yl)acetamide (200 mg).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. temperatureAfter being cooled
  3. customthe reaction mixture was decanted
  4. additionthe residue was poured into saturated aqueous sodium bicarbonate
  5. extractionThe mixture was extracted three times with ethyl acetate
  6. extractionThe combined extract
  7. dry with materialwas dried over magnesiumsulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resultant residue was triturated in ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-5140bfc7c37d46b7a083df14ca23ab2c
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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