Methylhydrazine sulfate → HCID 89979634, compound

HRID 517563Notes

Reaction equation

HRID 517563 reaction equation
[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]

Participants

5

Reactant 2

HCID 165286Methylhydrazine sulfateHCID 86711474HCID 86711474, compound

Product 2

HCID 86711504HCID 86711504, compoundYield 32%HCID 89979634HCID 89979634, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-9545778d774343e0852d7c46f9624628
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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