1,2-Dichloroethane → HCID 178438006, Verbindung

HRID 734700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734700
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[CH2:32][CH3:33].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[CH2:32]([C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([NH:22][C:8]([C:7]3[CH:6]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=4)[CH2:5][C:4](=[O:21])[NH:3][C:2]=3[CH3:1])=[O:9])[CH:24]=2)[NH:28][N:27]=1)[CH3:33]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178438005HCID 178438005, Verbindung

Produkt 1

HCID 178438006HCID 178438006, VerbindungAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of Example 1, Step 2 (50 mg, 0.178 mmol, 1.00 equiv), 5-amino-3-ethylindazole (29 mg, 0.178 mmol, 1.0 equiv), and EDC (41 mg, 0.213 mmol, 1.20 equiv) were suspended in 0.5 mL DMF. Et3N (0.030 mL, 0.213 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 flash chromatography (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (5-85% CH3CN/H2O—NH4OH to pH 10 over 10 minutes, retention time 6.32 min) to provide 17 mg (22%) of the title compound as a white solid. MS (ES+) m/e 425 [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 flash chromatography (20-100% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (5-85% CH3CN/H2O—NH4OH to pH 10 over 10 minutes, retention time 6.32 min)

Quellen und Nachweise

ORD-Eintrag
ord-3544097e1fda4ecf89caa31b32e1d93f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592357B2

Notizen zur Reaktion

Wird geladen…