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Ethyl chloroformate → methyl {6-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetate

HRID 1502211
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1502211
Cl[C:2](OCC)=[O:3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([Br:25])[C:17]=2[CH3:26])=[O:15])=[CH:10][C:9]=1[C:27]([NH:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:28]>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Br:25][C:18]1[C:17]([CH3:26])=[C:16]([C:14]([C:11]2[CH:10]=[C:9]3[C:8](=[CH:13][CH:12]=2)[NH:7][C:2](=[O:3])[N:29]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:27]3=[O:28])=[O:15])[N:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[CH:23]2
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Komponenten

6

Edukt 2

HCID 10928Ethyl chloroformateHCID 117776375methyl N-({2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]phenyl}carbonyl)glycinate

Produkt 1

HCID 89618502methyl {6-[(1-bromo-2-methylindolizin-3-yl)carbonyl]-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl}acetateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl chloroformate (1.3 mL; 13.5 mmol) is added dropwise to a solution of methyl N-({2-amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]phenyl}carbonyl)glycinate (2 g; 4.5 mmol) in 9 mL of pyridine at 0° C. After 15 min of stirring at ambient temperature, the reaction medium is concentrated to dryness and then diluted with ethyl acetate. The solution is washed with a 0.1 M hydrochloric acid solution and a saturated solution of sodium chloride, dried over sodium sulphate and concentrated to dryness. The yellow solid obtained is dissolved in 20 mL of anhydrous tetrahydrofuran and heated at reflux in the presence of diaza(1,3)bicyclo[5,4,0]undec-7-ene (1.35 mL; 9 mmol) for 1 h. The reaction medium is diluted with ethyl acetate, washed with a 0.1 M hydrochloric acid solution and a saturated solution of sodium chloride, dried over sodium sulphate and concentrated to dryness to give 2 g (95%) of a yellow powder.

Aufarbeitung

  1. concentrationthe reaction medium is concentrated to dryness
  2. additiondiluted with ethyl acetate
  3. washThe solution is washed with a 0.1 M hydrochloric acid solution
  4. dry with materiala saturated solution of sodium chloride, dried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. customThe yellow solid obtained
  7. temperatureheated
  8. washwashed with a 0.1 M hydrochloric acid solution
  9. dry with materiala saturated solution of sodium chloride, dried over sodium sulphate
  10. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-911292f8937f40cf979c4de90d3047bd
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09206177B2

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