Hydrochloric Acid → HCID 136337162, Verbindung

HRID 1428829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428829
Cl.O1CCOCC1.[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[N:27](COCC[Si](C)(C)C)[C:26](=[O:36])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH3:43])[CH:24]=3)[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]>>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:18]2[NH:27][C:26](=[O:36])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH3:43])[CH:24]=3)[N:19]=2)[CH:17]=1)=[O:12])[CH3:9]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68487879HCID 68487879, Verbindung

Produkt 1

HCID 136337162HCID 136337162, VerbindungAusbeute 80 %

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A solution of HCl in dioxane (4M, 0.872 mL, 3.48 mmol) was added to 1-[4-oxo-6-o-tolyl-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (88.0 mg, 0.174 mmol). The reaction mixture was stirred at 23° C. After 18 h, the reaction mixture was concentrated under reduced pressure. Et2O was added (5 mL) and the resulting precipitate was collected by filtration and washed well with Et2O to afford the titled compound (52.0 mg, 80%). MS (ESI): mass calcd. for C21H18N4O3, 374.1; m/z found 375.2 [M+H]+. 1H NMR (600 MHz, CDCl3): 9.05 (s, 1H), 8.35 (s, 1H), 8.02 (s, 1H), 7.86 (d, J=6.6 Hz, 1H), 7.78 (s, 1H), 7.37-7.28 (m, 4H), 4.31 (q, J=7.1 Hz, 2H), 2.28 (s, 3H), 1.33 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEt2O was added (5 mL)
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed well with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-8af44849201245d284057e3a83666583
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937078B2

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