Hydrochloric Acid → Febuxostat

HRID 870884노트

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HRID 870884 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[S:15][C:16]([C:20]([O:22]CC)=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].[OH-].[Na+].Cl>CC(C)=O>[CH3:19][C:17]1[N:18]=[C:14]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[C:3]([C:1]#[N:2])[CH:4]=2)[S:15][C:16]=1[C:20]([OH:22])=[O:21]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

생성물 1

HCID 134018Febuxostat수율 36.3%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
25 °C

실험 절차

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (3.0 g), acetone (30 mL), and 1 N sodium hydroxide solution (12 mL) were placed into a round bottom flask and heated to reflux. The mixture was maintained under reflux until reaction completion. After the reaction was completed, the mass was cooled to about 25° C. and the pH was adjusted to about 1 to 2 with hydrochloric acid (1.5 mL). The mass was extracted into ethyl acetate (40 mL). The ethyl acetate layer was washed with water (30 mL). The ethyl acetate layer was distilled completely under vacuum below 60° C. Acetone (30 mL) was added to the residue and the mixture was heated to reflux and maintained for about 30 minutes. The mass was then cooled to about 25° C., maintained for about 60 minutes, filtered under vacuum and the solid was washed with acetone (3 mL). The wet solid was dried at about 60° C. to a constant weight to yield 1.0 g of the title compound. Purity by HPLC: 99.5%.

후처리

  1. temperatureheated to reflux
  2. temperatureThe mixture was maintained
  3. temperatureunder reflux until reaction completion
  4. extractionThe mass was extracted into ethyl acetate (40 mL)
  5. washThe ethyl acetate layer was washed with water (30 mL)
  6. distillationThe ethyl acetate layer was distilled completely under vacuum below 60° C
  7. additionAcetone (30 mL) was added to the residue
  8. temperaturethe mixture was heated
  9. temperatureto reflux
  10. temperaturemaintained for about 30 minutes
  11. temperatureThe mass was then cooled to about 25° C.
  12. temperaturemaintained for about 60 minutes
  13. filtrationfiltered under vacuum
  14. washthe solid was washed with acetone (3 mL)
  15. customThe wet solid was dried at about 60° C. to a constant weight

출처 및 근거

ORD 기록
ord-254278f0d92e4418a655aea7239bf430
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969582B2

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