Water → HCID 86692501, compound

HRID 1748552Notes

Reaction equation

HRID 1748552 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:13]=[N:14][C:15]([CH:18]3[CH2:20][CH2:19]3)=[CH:16][CH:17]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].O>CO.O1CCCC1>[CH:18]1([C:15]2[N:14]=[CH:13][C:12]([N:9]3[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[CH:17][CH:16]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86692499HCID 86692499, compound

Product 1

HCID 86692501HCID 86692501, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(6-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (910 mg) in methanol (3 ml) and tetrahydrofuran (5 ml) were added 4 N aqueous solution of sodium hydroxide (7 ml) and water (3 ml), and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the layer to pH 5, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. To the obtained residue were added ethyl acetate and n-hexane, the precipitated solid was collected by filtration, washed with ethyl acetate/n-hexane solution, and heat-dried in vacuo at 60° C. to give the titled compound (321 mg) as a pale yellow solid. MS (ESI) m/z: 244 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated in vacuo
  3. additionwater and diethyl ether were added
  4. customthe aqueous layer was separated
  5. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  6. temperaturecooling
  7. extractionextracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated in vacuo
  10. additionTo the obtained residue were added ethyl acetate and n-hexane
  11. filtrationthe precipitated solid was collected by filtration
  12. washwashed with ethyl acetate/n-hexane solution
  13. customheat-dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-32ef4397810e42c9a0e7eb7ea890a91e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…