Water → 5-Cyclopropyl-3-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1011966Notes

Reaction equation

HRID 1011966 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=O)[C:6]([CH:8]1[CH2:10][CH2:9]1)=O)[CH3:2].Cl.[NH2:21][NH2:22].O.O1CCOCC1.Cl>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:21][NH:22][C:6]=1[CH:8]1[CH2:10][CH2:9]1)=[O:19])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 115031Hydrazinium chlorideHCID 204431481,4-Dioxane hydrochlorideHCID 673137573-Cyclopropyl-3-oxo-2-(pyridine-4-carbonyl)-propionic acid ethyl ester

Product 1

HCID 673149455-Cyclopropyl-3-pyridin-4-yl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg (0.84 mmol) of 3-cyclopropyl-3-oxo-2-(pyridine-4-carbonyl)-propionic acid ethyl ester and 57 mg (0.84 mmol) hydrazine.hydrochloride were dissolved in 3 ml ethanol, 1.5 ml water and 0.2 ml 4M HCl dioxane. The yellow solution was stirred 1 h at room temperature. The reaction mixture was evaporated, the residue taken in EtOAc and washed with brine, the aqueous layers were extracted with EtOAc. The combined organic phases were dried over magnesium sulfate and evaporated. The title compound was received as yellow gum (148 mg, 68%). MS: 258.0 (MH+).

Workup

  1. customThe reaction mixture was evaporated
  2. washwashed with brine
  3. extractionthe aqueous layers were extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d925056f02094571bc2da9bf7eb71658
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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