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Dimethylformamide → N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoro-methyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734718
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734718
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][C:16](=[O:18])[NH:15][C:14]([CH3:19])=[C:13]1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[Cl:34][C:35]1[C:43]2[C:38](=[CH:39][C:40]([F:45])=[C:41]([NH2:44])[CH:42]=2)[NH:37][N:36]=1>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O.Cl>[Cl:34][C:35]1[C:43]2[C:38](=[CH:39][C:40]([F:45])=[C:41]([NH:44][C:20]([C:13]3[CH:12]([C:3]4[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=4[F:1])[CH2:17][C:16](=[O:18])[NH:15][C:14]=3[CH3:19])=[O:21])[CH:42]=2)[NH:37][N:36]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 688271204-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

Produkt 1

HCID 178429200N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-[2-fluoro-4-(trifluoro-methyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide
Ausbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from Example 21, Step 2 (1.0 g, 3.152 mmol, 1.0 equiv) and oxalyl chloride (330 μL, 3.783 mmol, 1.2 equiv) in CH2Cl2 (12.5 mL) with catalytic DMF (20 μL) was stirred at room temperature for 45 minutes. The reaction mixture was concentrated en vacuo and half was redissolved in CH2Cl2 (5 mL). This solution was added dropwise over 5 minutes to a solution of the product from Example 39, step 2 (322 mg, 1.733 mmol, 1.1 equiv) in pyridine (4 mL) at −20° C. The reaction mixture was slowly warmed to room temperature over 3 hours. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was concentrated en vacuo. The residue was purified by flash chromatography (0-80% EtOAc in Hexanes) and further purified by reverse-phase HPLC (20-90% CH3CN/H2O, 0.1TFA over 13 minutes, retention time 8.11 min) to provide 60 mg (8%) of the title compound as a white solid. MS (ES+) m/e 485 [M+H]+

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated en vacuo and half
  2. dissolutionwas redissolved in CH2Cl2 (5 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed twice with 1N HCl, once with satd
  5. concentrationThe organic phase was concentrated en vacuo
  6. customThe residue was purified by flash chromatography (0-80% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (20-90% CH3CN/H2O, 0.1TFA over 13 minutes, retention time 8.11 min)

Quellen und Nachweise

ORD-Eintrag
ord-a89d76ddb91542ec99d1e9f520c60883
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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