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1,2-Dichloroethane → N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734705
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][N:22]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH:30][C:16]([C:9]3[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[F:19])[CH2:13][C:12](=[O:14])[NH:11][C:10]=3[CH3:15])=[O:18])[CH:28]=2)[NH:23][N:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

Produkt 1

HCID 178429202N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide
Ausbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of Example 3 Step 2 (191 mg, 0.668 mmol, 1.00 equiv), the product of Step 2 (125 mg, 0.668 mmol, 1.0 equiv), and EDC (153 mg, 0.802 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.112 mL, 0.802 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. 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 dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min) to provide 20 mg (7%) of the title compound as a white solid. MS (ES+) m/e 452 [M+H]+

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min)

Quellen und Nachweise

ORD-Eintrag
ord-8d585ffb8f87406eb6d71dbecbadcc4d
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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