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

HRID 1897745Notes

Reaction equation

HRID 1897745 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-9396913b99334f9980762f688d72a05a
Source dataset
uspto-grants-2013_08
Patent number
US08519151B2

Reaction notes

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