N,N'-Dimethylethylenediamine → N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide

HRID 1897745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1897745
C([O-])([O-])=O.[K+].[K+].[F:7][CH:8]([F:18])[C:9]1[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]([CH3:17])[N:10]=1.Br[C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]1[C:30](=[C:31]([Cl:33])[Cl:32])[CH:25]2[CH2:24][CH2:23]1.CNCCNC>>[Cl:32][C:31]([Cl:33])=[C:30]1[CH:22]2[C:21]3[C:26]([CH:25]1[CH2:24][CH2:23]2)=[CH:27][CH:28]=[CH:29][C:20]=3[NH:16][C:14]([C:13]1[C:9]([CH:8]([F:7])[F:18])=[N:10][N:11]([CH3:17])[CH:12]=1)=[O:15]

Komponenten

5

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 469283513-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideHCID 534926965-Bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene

Produkt 1

HCID 53491464N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide

Versuchsvorschrift

A 20 ml screw-cap vial was filled with the following solids: CuO (0.05 mmol, 4.0 mg), anhydrous CuCl2 (0.05 mmol, 6.7 mg), K2CO3 (2.0 mmol, 277 mg), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide (1.1 mmol, 193 mg) and 5-bromo-9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalene (1.0 mmol, 304 mg). A magnetic stir bar was added, and the open vial was gently flushed with N2. Dioxane (2 mL) was added, followed by N,N′-dimethylethylenediamine (0.45 mmol, 48 μl). The vial was sealed and placed into a preheated screening block at 130° C. Conversion was complete after 24 hours. The yield (HPLC-analysis) of the compound of formula I was 70%.

Aufarbeitung

  1. customA 20 ml screw-cap vial
  2. additionwas filled with the following solids
  3. additionA magnetic stir bar was added
  4. customthe open vial was gently flushed with N2
  5. additionDioxane (2 mL) was added
  6. customThe vial was sealed
  7. customplaced into a preheated screening block at 130° C
  8. customThe yield (HPLC-analysis) of the compound of formula I

Quellen und Nachweise

ORD-Eintrag
ord-9396913b99334f9980762f688d72a05a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519151B2

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