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Dimethyl Sulfoxide → 7-[(2,3-Difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486284
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HRID 1486284 반응식
C([O:3][C:4]([C:6]1[C:7]([CH3:26])=[N:8][N:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=3[F:24])=[CH:13][C:12]([CH3:25])=[CH:11][C:10]=12)=[O:5])C.[OH-].[Na+].CS(C)=O>O1CCOCC1>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:14]1[N:9]2[N:8]=[C:7]([CH3:26])[C:6]([C:4]([OH:5])=[O:3])=[C:10]2[CH:11]=[C:12]([CH3:25])[CH:13]=1
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참가 물질

5

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HCID 679Dimethyl SulfoxideHCID 14798Sodium Hydroxide2회HCID 1178645947-[(2,3-Difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl Ester

생성물 1

HCID 1178597477-[(2,3-Difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A solution of 190 mg (0.527 mmol) of 7-[(2,3-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester from Example 116A in 5 ml of dioxane was admixed with 2.1 ml of 2 N sodium hydroxide solution. The resulting mixture was stirred at 90° C. for 15 h. Owing to incomplete mixing, 1 ml of dimethyl sulphoxide was added, followed by further 2 N sodium hydroxide solution (1 ml). The resulting mixture was stirred for a further 2 h. After the reaction had ended, the solvent was removed under reduced pressure. The residue was admixed with acetonitrile (5 ml), followed by the dropwise addition of trifluoroacetic acid (2 ml). The resulting precipitate was filtered off and dried under reduced pressure, which gave 130 mg (71% of theory, 93% pure) of the target compound.

후처리

  1. stirringThe resulting mixture was stirred for a further 2 h
  2. customthe solvent was removed under reduced pressure
  3. additionfollowed by the dropwise addition of trifluoroacetic acid (2 ml)
  4. filtrationThe resulting precipitate was filtered off
  5. customdried under reduced pressure, which
  6. customgave 130 mg (71% of theory, 93% pure) of the target compound

출처 및 근거

ORD 기록
ord-76da97ba07a24d34884e9341d050e512
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09422285B2

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