Methylhydrazine sulfate → N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 517563ノート

反応式

HRID 517563 の反応式
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([C:15](OCC)=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1.S(O)(O)(=O)=O.[CH3:27][NH:28][NH2:29]>CCO>[CH3:27][NH:28][NH:29][C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:21])([F:20])[F:1])=[CH:5][CH:6]=2)[N:14]=1)=[O:16].[CH3:27][N:28]([C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:21])([F:20])[F:1])=[CH:5][CH:6]=2)[N:14]=1)=[O:16])[NH2:29]

参加物

5

反応物 2

HCID 165286Methylhydrazine sulfateHCID 86711474Ethyl 3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylate

生成物 2

HCID 86711504N'-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide収率 32%HCID 89979634N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide収率 34%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (3.5 g, 11.5 mmol) in EtOH (25 mL), methylhydrazine sulfate salt (2.5 g, 17.2 mmol) and TEA (7.5 mL) were added at RT. The mixture was stirred at RT overnight, concentrated and purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA) to give N′-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide (1.1 g, 32%) and N-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide as white solids (1.2 g, 34%). MS (ES+) C11H9F3N4O3 requires: 302, found: 303[M+H]+.

後処理

  1. concentrationconcentrated
  2. custompurified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA)

出典と根拠

ORDレコード
ord-9545778d774343e0852d7c46f9624628
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

反応ノート

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