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1,2-Dichloroethane → HCID 178429201, Verbindung

HRID 734719
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734719
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][C:24](=[O:26])[NH:23][C:22]([CH3:27])=[C:21]2[C:28](O)=[O:29])=[CH:16][CH:15]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH:11][C:28]([C:21]3[CH:20]([C:17]4[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=4)[CH2:25][C:24](=[O:26])[NH:23][C:22]=3[CH3:27])=[O:29])[CH:9]=2)[NH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 534357904-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

Produkt 1

HCID 178429201HCID 178429201, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from Example 39, Step 2 (210 mg, 1.129 mmol, 1.0 equiv) was combined with the product from Example 4, Step 2 (300 mg, 1.129 mmol, 1.0 equiv), EDC (260 mg, 1.355 mmol, 1.2 equiv) and Et3N (189 μL, 1.355 mmol, 1.2 equiv) in DMF (3 mL) and stirred at room temperature for 18 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 (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (17-90% CH3CN/H2O, 0.1% TFA over 13 minutes, retention time 7.5 min) to provide 125 mg (26%) of the title compound as a white solid. MS (ES+) m/e 434 [M+H]+

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. concentrationThe organic phase was concentrated en vacuo
  4. customThe residue was purified by flash chromatography (20-100% EtOAc in Hexanes)
  5. customfurther purified by reverse-phase HPLC (17-90% CH3CN/H2O, 0.1% TFA over 13 minutes, retention time 7.5 min)

Quellen und Nachweise

ORD-Eintrag
ord-f5377d31c43d4d42adda60a77a91cdd7
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592357B2

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