Triethylamine → N-(2-bromo-4,6-difluorophenyl)-1-(3-chloro-2-pyridinyl)-3-bromo-1H-pyrazole-5-carboxamide

HRID 2354935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354935
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:9]=1.C(N(CC)CC)C.[Br:30][C:31]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[C:32]=1[NH2:33]>CN(C)C=O.C(Cl)Cl.CN(C)C1C=CN=CC=1.C(=O)=O>[Br:30][C:31]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[C:32]=1[NH:33][C:13]([C:11]1[N:10]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:9]=[C:8]([Br:7])[CH:12]=1)=[O:15]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1362852-Bromo-4,6-DifluoroanilineHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid2×

Produkt 1

HCID 11684615N-(2-bromo-4,6-difluorophenyl)-1-(3-chloro-2-pyridinyl)-3-bromo-1H-pyrazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 280Carbon DioxideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (0.043 mL, 0.5 mmol) was added to a mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. the product of Step D) (200 mg, 0.66 mmol) and two drops of N,N-dimethylformamide (DMF) in 30 mL of methylene chloride at room temperature and the reaction was stirred for 10 minutes. After this time a catalytic amount of 4-(dimethylamino)pyridine was added, followed by dropwise addition of a mixture of triethylamine (184 mL, 1.4 mmol) and 2-bromo-4,6-difluoroaniline in 10 mL of methylene chloride. The reaction was stirred overnight and then concentrated to near dryness. Chromatography on silica gel with hexane/ethyl acetate gradient as eluent (9:1 to 1:1) afforded an oil. The oil was then cooled in dry ice and triturated with ether/hexane to provide the title compound (0.22 g), a compound of the present invention, as a solid melting at 138-139° C.

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated
  3. customChromatography on silica gel with hexane/ethyl acetate gradient as eluent (9:1 to 1:1) afforded an oil
  4. customtriturated with ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9bcfae33e6d94cdd864dbc3ee2a0e907
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754738B2

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