Triethylamine → HCID 53654615, compound

HRID 1655178Notes

Reaction equation

HRID 1655178 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10](Cl)=[O:11])#[N:2].[CH2:24]([N:26](CC)[CH2:27]C)C.Cl.CNC>O1CCCC1>[CH3:24][N:26]([CH3:27])[C:10](=[O:11])[CH:9]=[CH:8][C:7]1[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[N:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 53679607HCID 53679607, compound

Product 1

HCID 53654615HCID 53654615, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.5 gram (0.001 mole) of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid chloride and 1.3 grams (0.012 mole) of triethylamine in 100 mL of tetrahydrofuran was added 1.0 gram (0.012 mole) of dimethylamine hydrochloride. Upon completion of the addition, the reaction was stirred at ambient temperature for about 18 hours. The reaction mixture was then warmed to 65° C. Where it was stirred for 15 minutes. The reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was dissolved in ethyl acetate, and the solution was washed with water. The organic layer was treated with decolorizing carbon and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was triturated with petroleum ether, and a solid was collected by filtration, yielding 0.2 gram of N,N-dimethyl-3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylamide; m.p. 116°-120° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. temperatureThe reaction mixture was then warmed to 65° C
  3. stirringWhere it was stirred for 15 minutes
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated under reduced pressure to a residue
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washthe solution was washed with water
  8. additionThe organic layer was treated with decolorizing carbon
  9. dry with materialdried with magnesium sulfate
  10. filtrationThe mixture was filtered
  11. concentrationthe filtrate was concentrated under reduced pressure to a residue
  12. customThe residue was triturated with petroleum ether
  13. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-4e055962bdfc4fb39107042f31249389
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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