Water → HCID 22449795, compound

HRID 2187058Notes

Reaction equation

HRID 2187058 reaction equation
[NH2:1][C:2]1[N:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4](NCC1C=CC(OC)=CC=1)=O.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].[OH2:26].[CH3:27][CH2:28][O-:29].[Na+].N1C=C[CH:34]=[CH:33][CH:32]=1>>[O:26]=[C:2]1[N:1]([C:33]([CH3:34])([CH3:32])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:28](=[O:29])[C:27]2[C:18](=[CH:17][CH:16]=[CH:3][CH:4]=2)[NH:19]1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 2723922Sodium ethoxideHCID 224497462-Amino-N-[(4-methoxyphenyl)methyl]-3-pyridinecarboxamide

Product 1

HCID 22449795HCID 22449795, compoundYield 85%

Procedure

(Method 2) Ethyl 2-(2-aminobenzamide)isobutyrate (6.98 g, 27.9 mmol) obtained in Reference Example 19 was dissolved in pyridine (30 ml) and treated dropwise with ethyl chloroformate (2.94 ml, 30.7 mmol) with cooling on ice and stirring. The reaction mixture was stirred at room temperature for 2 hours, combined with water and then extracted with ethyl acetate. The extract was washed with an aqueous solution of potassium hydrogen sulfate followed by saturated brine, and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The residue was taken up with ethanol (150 ml) and combined with sodium ethylate (2.09 g, 30.7 mmol) and heated under reflux for 15 hours. The solvent was distilled off under reduced pressure and the residue was diluted with water and neutralized with 1N hydrochloric acid. The crystal precipitated was recovered by filtration to give the title compound (6.57 g, 85%) as a colorless crystal.

Workup

  1. temperaturewith cooling on ice
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of potassium hydrogen sulfate
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off under reduced pressure
  7. temperatureheated
  8. temperatureunder reflux for 15 hours
  9. distillationThe solvent was distilled off under reduced pressure
  10. additionthe residue was diluted with water and neutralized with 1N hydrochloric acid
  11. customThe crystal precipitated
  12. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-e87c01b53eb843ffaf967234d6c00294
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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