Pyridine → 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one

HRID 245641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245641
[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:15][C:16]1[C:17]([N:22]2[C:26]([C:27](O)=O)=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>O1CCCC1>[Cl:15][C:16]1[C:17]([N:22]2[C:26]([C:27]3[O:13][C:12](=[O:14])[C:11]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][N:9]=5)[CH:4]=[CH:3][C:2]=4[N:1]=3)=[CH:25][C:24]([C:30]([F:33])([F:31])[F:32])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 579901777-Amino-quinoline-8-carboxylic acid

Produkt 1

HCID 579901522-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-oneAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 500 mg (2.66 mmol) of 7-amino-quinoline-8-carboxylic acid in 20 mL of anhydrous tetrahydrofuran at 10° C., is added 775 mg (2.66 mmol) of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid followed by 1.07 mL (13.28 mmol) of pyridine. Then the suspension is cooled to 0° C. and 830 μL (10.63 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at ambient temperature for 48 hours. Then the solvent is evaporated and the residue is precipitated with a minimum of water. The filtration gave 180 mg of product after drying on high vacuum pump. The filtrate is evaporated and the residue obtained is purified by flash chromatography to afford 100 mg more of product as a solid. The overall yield is 24%; LC/MS:444/446 (M+H)+.

Aufarbeitung

  1. customThen the solvent is evaporated
  2. customthe residue is precipitated with a minimum of water
  3. filtrationThe filtration

Quellen und Nachweise

ORD-Eintrag
ord-73c2a5a34ebf44958f58d986c560af06
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658801B2

Notizen zur Reaktion

Wird geladen…