Triethylamine → Methyl 2-({[2-(dimethylamino)-2-oxoethyl]carbamoyl}amino)-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

HRID 535442

Reaktionsgleichung

Reaktionsgleichung von HRID 535442
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:34]3[C:29]([CH:30]=[CH:31][CH:32]=[CH:33]3)=[C:28]([O:35][CH3:36])[C:27]=2[CH3:37])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(O)(=O)C.[CH3:42][N:43]([CH3:48])[C:44](=[O:47])[CH2:45][NH2:46].C(N(CC)CC)C>O1CCOCC1.O>[CH3:42][N:43]([CH3:48])[C:44](=[O:47])[CH2:45][NH:46][C:2]([NH:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:34]3[C:29]([CH:30]=[CH:31][CH:32]=[CH:33]3)=[C:28]([O:35][CH3:36])[C:27]=2[CH3:37])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:4]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 533990092-Amino-N,N-dimethylacetamide acetateHCID 66653263Methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

Produkt 1

HCID 66652958Methyl 2-({[2-(dimethylamino)-2-oxoethyl]carbamoyl}amino)-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoateAusbeute 143,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

0.798 g (2.69 mmol) of triphosgene diluted in 10 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 1.3 g (3.84 mmol) of methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate in 50 ml of dioxane. After stirring for 1 hour, 1.25 g (7.68 mmol) of N,N-dimethylglycinamide acetate and 2.68 ml (19.21 mmol) of triethylamine are added. The reaction medium is stirred overnight at ambient temperature and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is dried over sodium sulphate, filtered, and then concentrated under reduced pressure. 1.8 g of a yellow solid are obtained.

Aufarbeitung

  1. stirringThe reaction medium is stirred overnight at ambient temperature
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customThe organic phase obtained
  4. dry with materialis dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7fe39e2e149f470199cb02595e447c39
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859544B2

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