Pyridine → HCID 22013556, compound

HRID 1532578Notes

Reaction equation

HRID 1532578 reaction equation
[F:1][C:2]1[C:3]([C:9]2[C:13]([CH3:14])=[C:12]([C:15](=O)[NH2:16])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1>[F:1][C:2]1[C:3]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22013571HCID 22013571, compound

Product 1

HCID 22013556HCID 22013556, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
22 °C

Procedure

1.82 g of 3-(3-fluoro-5-chloro-2-pyridyl)-4-methyl-5-carbamoyl-1-methyl-[1H]-pyrazole (Example H44) are suspended in 20 ml of dioxane. First 1.65 ml of pyridine and then 1.44 ml of trifluoroacetic anhydride are added, while cooling in an ice-bath. 5 minutes later, the cooling bath is removed and the mixture is stirred at 22° C. for 1 hour. The brown-red solution is diluted with diethyl ether and washed with one molar hydrochloric acid and then with brine. After drying over sodium sulfate and filtering, the filtrate is concentrated directly together with twice the amount of silica gel. After application of this silica gel to a flash column, the column is eluted with n-hexane/ethyl acetate 4/1. 1.60 g of the desired title compound are obtained as a beige solid of melting point 144-146° C.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. custom5 minutes later, the cooling bath is removed
  3. additionThe brown-red solution is diluted with diethyl ether
  4. washwashed with one molar hydrochloric acid
  5. dry with materialAfter drying over sodium sulfate
  6. filtrationfiltering
  7. concentrationthe filtrate is concentrated directly together with twice the amount of silica gel
  8. washAfter application of this silica gel to a flash column, the column is eluted with n-hexane/ethyl acetate 4/1

Sources & evidence

ORD record
ord-2d4e2065f1424bb7a6c859231425c784
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Reaction notes

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