Dicyclohexylcarbodiimide → Ethyl 3-imino-5-methoxy-2,3-dihydroimidazo[1,5-a]pyridine-7-carboxylate

HRID 249734

Reaktionsgleichung

Reaktionsgleichung von HRID 249734
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[N:9]=[C:8]([CH2:14][NH:15][C:16]([NH:18]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=S)[CH:7]=1)=[O:5])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1>C1(C)C=CC=CC=1>[NH:18]=[C:16]1[N:9]2[C:10]([O:12][CH3:13])=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][C:8]2=[CH:14][NH:15]1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 57791304N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea

Produkt 1

HCID 178469329Ethyl 3-imino-5-methoxy-2,3-dihydroimidazo[1,5-a]pyridine-7-carboxylateAusbeute 15,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.17 g (2.38 mmol) of N-(4-ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N′-(fluoren-9-ylmethyloxycarbonyl)thiourea (20e) were treated with 491 mg (2.38 mmol) of DCC in 25 ml of toluene and refluxed for six hours. After standing overnight at RT, the mixture was freed from the solvent and the residue was chromatographed on silica gel (heptane/ethyl acetate 75:25→ethyl acetate/methanol 90:10), it being possible to isolate 88 mg of the title compound.

Aufarbeitung

  1. temperaturerefluxed for six hours
  2. customthe residue was chromatographed on silica gel (heptane/ethyl acetate 75:25→ethyl acetate/methanol 90:10), it

Quellen und Nachweise

ORD-Eintrag
ord-26a9d4dd61c04d089dbadc506405d775
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863269B2

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