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

HRID 249734

Reaction equation

HRID 249734 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 178469329Ethyl 3-imino-5-methoxy-2,3-dihydroimidazo[1,5-a]pyridine-7-carboxylateYield 15.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-26a9d4dd61c04d089dbadc506405d775
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

Loading…