Formic Acid → 4-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylic acid

HRID 1617610ノート

反応式

HRID 1617610 の反応式
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[F:36])[CH2:18]/[C:19](=[N:27]\[OH:28])/[C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C.[Li+].[OH-].C(O)=O>O1CCOCC1.O>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([CH:17]([C:14]2[CH:13]=[CH:12][C:11]([C:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][CH:8]=3)=[CH:16][CH:15]=2)[CH2:18]/[C:19](=[N:27]\[OH:28])/[C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=2)=[C:30]([F:36])[CH:31]=1

参加物

5

反応物 3

HCID 284Formic AcidHCID 3939Lithium Hydroxide2 回HCID 136167036ethyl 4-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylate

生成物 1

HCID 1361669614-[4-[(3E)-1-(4-chloro-2-fluorophenyl)-3-hydroxyimino-3-(2-methyl-4-pyridinyl)propyl]phenyl]thiophene-2-carboxylic acid収率 98.6%

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-{4-[1-(4-chloro-2-fluoro-phenyl)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-propyl]-phenyl}-thiophene-2-carboxylic acid ethyl ester (15 mg) in dioxane/water (1.5 mL, 1:1) was added LiOH (7.2 mg) and the reaction mixture heated by microwave irradiation to 100° C. for 30 min. Formic acid was added to neutralize LiOH and the solvent mixture removed by evaporation under reduced pressure. Purification of the crude reaction product by silica column chromatography eluting with a mixture of dichloromethane/methanol (95:5, containing 4% formic acid) provided 14 mg (98%) of the title compound as an off-white powder, MS (ESI+): m/z=495.1 [M+H]+.

後処理

  1. customthe solvent mixture removed by evaporation under reduced pressure
  2. customPurification of the crude
  3. customreaction product by silica column chromatography
  4. washeluting with a mixture of dichloromethane/methanol (95:5, containing 4% formic acid)

出典と根拠

ORDレコード
ord-adb77e2479554683b7bd2a20b6c8a17d
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

反応ノート

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