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

HRID 517563노트

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HRID 517563 반응식
[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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-9545778d774343e0852d7c46f9624628
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115120B2

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