Trimethyl orthovalerate → HCID 69506740, Verbindung

HRID 2366727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366727
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:22](OC)(OC)(OC)[CH2:23][CH2:24][CH2:25][CH3:26].C(OC)(OC)(OC)CCC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>>[CH2:23]([C:22]1[N:12]([CH2:13][C:14]([CH3:20])([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:24][CH2:25][CH3:26]

Komponenten

5

Edukt 4

HCID 83755Trimethyl orthovalerate2×HCID 1235121,1,1-TrimethoxybutaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447056HCID 57447056, Verbindung

Produkt 1

HCID 69506740HCID 69506740, Verbindung

Versuchsvorschrift

Ethyl 3-(3-aminoquinolin-4-ylamino)-2,2-dimethylpropanoate (see Example 26 Parts A through D, 9.0 g, 31.3 mmol) was treated according to a modification of the method described in Part B of Example 8 using trimethyl orthovalerate in lieu of trimethyl orthobutyrate. Prior to the addition of trimethyl orthovalerate (6.1 mL, 35 mmol) and pyridinium p-toluenesulfonate (0.050 g), the reaction was heated at reflux for 15 minutes and then cooled slightly. The reaction was heated at reflux for five hours, allowed to cool to ambient temperature, stirred overnight, and concentrated under reduced pressure to provide 11.2 g of ethyl 3-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanoate.

Aufarbeitung

  1. additionwas treated
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 15 minutes
  4. temperaturecooled slightly
  5. temperatureThe reaction was heated
  6. temperatureat reflux for five hours
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a73e0d67db6149efa61dd8c8aba3282b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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