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

HRID 1486284
ノート
印刷プレビュー

反応式

HRID 1486284 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium Hydroxide2 回HCID 1178645947-[(2,3-Difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl Ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76da97ba07a24d34884e9341d050e512
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422285B2

反応ノート

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