Sodium Hydroxide → HCID 67463041, compound

HRID 2043787Notes

Reaction equation

HRID 2043787 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[N:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:26]([F:29])([F:27])[F:28])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67460233HCID 67460233, compound2×

Product 1

HCID 67463041HCID 67463041, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-2H-1,2,3-triazole-4-carboxylate (0.35 g, 0.82 mmol) (i.e. the product of Example 32, Step B) was dissolved in a mixture of methanol (5 mL) and tetrahydrofuran (2 mL). A 1 N aqueous solution of sodium hydroxide (1.6 mL, 1.6 mmol) was added to the reaction mixture and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in water. The aqueous layer was washed with diethyl ether and the aqueous layer was acidified with concentrated hydrochloric acid to pH 1, and extracted with dichloromethane and then chloroform. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford 0.27 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. washThe aqueous layer was washed with diethyl ether
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b9bd801761f47dea1df78201cf17ddf
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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