HCID 18358864, compound → HCID 23293563, compound

HRID 428444Notes

Reaction equation

HRID 428444 reaction equation
[C:1]1([C:7]2[C:11]([C:12](=[O:21])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[NH2:20])=[C:10]([C:22](OCC)=[O:23])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C=CC=CN=1>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]2[C:12](=[O:21])[C:11]3[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:8][NH:9][C:10]=3[C:22](=[O:23])[NH:20][C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 18358864HCID 18358864, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 23293563HCID 23293563, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3-phenyl-4-(4-chloro-2-aminobenzoyl)-1H-pyrazole-5-carboxylate (0.84 g, 2.28 mmol) and 2-hydroxypyridine (0.217 g, 2.28 mmol) in toluene (12 mL) was distilled at 160° C. until all the toluene was removed. The residue was heated at the same temperature for 18 hours. The reaction residue was washed with water to remove the 2-hydroxypyridine. The insoluble material was added to methanol (225 mL) and heated to boiling. Ethyl acetate (100 mL) was added and the solution heated for an additional 2 minutes, then concentrated to 100 mL. The solution was filtered to remove some insoluble material and the filtrate concentrated via rotovap until a precipitate formed which was filtered to give the title compound as a tan solid (0.381 g, 51%, mp 328.1-330.9° C.).

Workup

  1. distillationwas distilled at 160° C. until all the toluene
  2. customwas removed
  3. temperatureThe residue was heated at the same temperature for 18 hours
  4. washThe reaction residue was washed with water
  5. customto remove the 2-hydroxypyridine
  6. additionThe insoluble material was added to methanol (225 mL)
  7. temperatureheated to boiling
  8. additionEthyl acetate (100 mL) was added
  9. temperaturethe solution heated for an additional 2 minutes
  10. concentrationconcentrated to 100 mL
  11. filtrationThe solution was filtered
  12. customto remove some insoluble material
  13. concentrationthe filtrate concentrated via rotovap until a precipitate
  14. customformed which
  15. filtrationwas filtered

Sources & evidence

ORD record
ord-65c415f67c904359afe698c9ffc33829
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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