Dimethylformamide dimethyl acetal → HCID 178497299, compound

HRID 861052Notes

Reaction equation

HRID 861052 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15](C(N)=O)[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.C[O:23][CH:24]([O:28][CH3:29])N(C)C>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:24]([O:28][CH3:29])=[O:23])[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178513567HCID 178513567, compound

Product 1

HCID 178497299HCID 178497299, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxamide prepared as set forth in Example A-223 (2.9 g, 0.01 mol) in 50 mL of methanol was added N,N-dimethylformamide dimethyl acetal (3.67 g, 0.03 mol) dropwise. The reaction mixture was stirred at room temperature overnight and heated at reflux for 4 hours. After cooling, the precipitate was collected by filtration and air-dried to give 2.0 g of methyl 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylate as a white solid (69% yield), mp: 239–241° C. Anal. Calc'd for C16H12FN3O2: C, 64.64; H, 4.07; N, 14.13. Found: C, 64.36; H, 4.10; N, 14.27.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. temperatureAfter cooling
  5. filtrationthe precipitate was collected by filtration
  6. customair-dried

Sources & evidence

ORD record
ord-363bc33d2362433784de22d7cdfe0748
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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