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

HRID 1897748노트

반응식

HRID 1897748 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-34c223e069564fcd829feb4c92bb706e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519152B2

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