Pyridine → N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748688

Reaktionsgleichung

Reaktionsgleichung von HRID 1748688
C1(C)C=CC=CC=1.[CH3:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)[N:12]=[CH:11][C:10]=1[C:24](Cl)=[O:25].[N:27]1C=CC=CC=1.[NH2:33][C:34]1[CH:35]=C[C:37]([Cl:40])=[N:38][CH:39]=1>O>[Cl:40][C:37]1[N:27]=[CH:35][C:34]([NH:33][C:24]([C:10]2[CH:11]=[N:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=3)[C:9]=2[CH3:8])=[O:25])=[CH:39][N:38]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 1140TolueneHCID 793055-Amino-2-chloropyridineHCID 897349975-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

Produkt 1

HCID 86692639N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Toluene (5 ml) was added to 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride (500 mg) described in Reference Example 180, pyridine (5 ml) and 5-amino-2-chloropyridine (198 mg) were added thereto with stirring, and the mixture was stirred at 80° C. for two hours. After completion of the reaction, water was added to the reaction solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (410 mg) as a white solid.

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred at 80° C. for two hours
  3. additionwas added to the reaction solution
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-193394df043047bcb842cd98228ef49b
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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