Trifluoroacetic acid → HCID 68519389, compound

HRID 1863947Notes

Reaction equation

HRID 1863947 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]([C:8]1[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=1)=[O:7].FC(F)(F)C(O)=O>ClCCl>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:9]=[C:8]2[C:6](=[O:7])[NH:5][CH:4]=[CH:3][N:12]2[N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178495997HCID 178495997, compound

Product 1

HCID 68519389HCID 68519389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 267 mg (1 mmol) of N-(2,2-dimethoxyethyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 1.6 mL of trifluoroacetic acid, and 1.6 mL of dichloromethane was stirred at room temperature overnight and then concentrated. The residue was suspended in polyphosphoric acid (enough to cover it) and heated at 145° C. for 4.5 h. The cooled mixture was treated with ice, and the pH was adjusted to 8-9 by addition of concentrated ammonium hydroxide solution. The mixture was transferred to a separatory funnel and shaken with dichloromethane. The organic phase was separated, and the aqueous phase was extracted twice more with dichloromethane. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to yield the title compound as a solid.

Workup

  1. concentrationconcentrated
  2. temperatureheated at 145° C. for 4.5 h
  3. additionThe cooled mixture was treated with ice
  4. additionthe pH was adjusted to 8-9 by addition of concentrated ammonium hydroxide solution
  5. customThe mixture was transferred to a separatory funnel
  6. stirringshaken with dichloromethane
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was extracted twice more with dichloromethane
  9. dry with materialThe combined organic fractions were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-be35d57baf2544bba8f2195328529ada
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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