Triethylamine → 5-methyl-1-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-1H-pyrazole-4-carboxylic acid pyridazin-4-ylamide

HRID 1496638

Reaktionsgleichung

Reaktionsgleichung von HRID 1496638
[CH3:1][C:2]1[N:6]([CH:7]([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[C:16](Cl)=[O:17].[N:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][N:20]=1.C(N(CC)CC)C>C(Cl)Cl.C(OC(=O)C)C>[N:19]1[CH:24]=[CH:23][C:22]([NH:25][C:16]([C:3]2[CH:4]=[N:5][N:6]([CH:7]([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])[C:2]=2[CH3:1])=[O:17])=[CH:21][N:20]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2984924-AminopyridazineHCID 891573995-Methyl-1-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyrazole-4-carbonyl chloride

Produkt 1

HCID 891570525-methyl-1-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-1H-pyrazole-4-carboxylic acid pyridazin-4-ylamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

A solution of 398 mg 5-methyl-1-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyrazole-4-carbonyl chloride in 10 ml CH2Cl2 was added dropwise to a solution of 185 mg pyridazin-4-amine and 750 mg triethylamine in 30 ml CH2Cl2 at 0° C. The mixture was stirred at 20-25° C. for about 68 h, diluted with 25 ml ethylacetate, washed with 3×15 ml sat. aq. NH4Cl solution, dried over MgSO4 and evaporated. Purification by flash chromatography (CH2Cl2/MeOH) gave 160 mg of the title compound (90% purity). HPLC-MS (Method 1): RT 2.278 min, m/z [MH]+ 354.1.

Aufarbeitung

  1. washwashed with 3×15 ml sat. aq. NH4Cl solution
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography (CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-88b83d26ba4340d3a383441a52ae6a09
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09198422B2

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