Trifluoroacetic acid → 5-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1024319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024319
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([NH:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=2)[CH:9]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 114773-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 13248993methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 576194175-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-Amino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (644, 1.3 g, 8.0 mmol) was combined with 3-chlorobenzaldehyde (645, 0.95 mL, 8.4 mmol) and acetonitrile (40 mL). Trifluoroacetic acid (3.2 mL, 42.0 mmol) was added followed by triethylsilane (6.7 mL, 42.0 mmol). The reaction was heated to reflux overnight and then concentrated. Ethyl acetate was added and the solution was washed with 1N potassium carbonate. The organic portion was dried over anhydrous sodium sulfate, filtered and concentrated. The compound (646, 0.944 g, 42%) was crystallized from a mixture of ethyl acetate:hexane.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionEthyl acetate was added
  5. washthe solution was washed with 1N potassium carbonate
  6. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe compound (646, 0.944 g, 42%) was crystallized from a mixture of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1de95e691942413cbb01a03d9af0a4f8
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722702B2

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