Dimethylformamide → N-[6-(4-Hydroxycyclohex-1-en-1-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748627
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][N:8]([CH3:11])C=O.[CH3:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[N:16]=[CH:15][C:14]=1[C:28]([OH:30])=O>ClCCl>[OH:5][CH:1]1[CH2:2][CH2:23][C:22]([C:11]2[N:8]=[CH:7][C:15]([NH:16][C:28]([C:14]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][N:19]=4)[C:13]=3[CH3:12])=[O:30])=[CH:14][C:13]=2[CH3:12])=[CH:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 162278455-methyl-1-(5-(trifluoromethyl)pyridin-2-yl)-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 56961707N-[6-(4-Hydroxycyclohex-1-en-1-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (0.20 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (175 mg) described in Reference Example 8 in dichloromethane (10 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, and toluene (10 ml) was added to the resulted reaction mixture. Next, a solution of 4-(5-amino-3-methylpyridin-2-yl)cyclohex-3-en-1-ol (120 mg) described in Reference Example 111 in pyridine (10 ml) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction, 1N aqueous solution of sodium hydroxide was added under ice-cooling and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with a silica gel column chromatography (chloroform/methanol), washed with ethanol, the resulting solid was filtered and dried at 60° C. in vacuo to give the titled compound (146 mg) as a white solid.

Aufarbeitung

  1. customThe solvent and an excess amount of oxalyl chloride were evaporated
  2. additiontoluene (10 ml) was added to the resulted reaction mixture
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature overnight
  6. customAfter the reaction, 1N aqueous solution of sodium hydroxide
  7. additionwas added under ice-
  8. temperaturecooling
  9. extractionextracted with chloroform
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe resulting residue was purified with a silica gel column chromatography (chloroform/methanol)
  13. washwashed with ethanol
  14. filtrationthe resulting solid was filtered
  15. customdried at 60° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-381341cdedbb4a6d8f01254c289a54b3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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