Ethyl isocyanate → HCID 24771485, compound

HRID 1670701Notes

Reaction equation

HRID 1670701 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:25]([CH:26]=1)[C:8]1[N:9]([C:18]3[CH:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[C:10](=[O:17])[C:11]3[C:16]([C:7]=1[N:6]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3.[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28]>C(Cl)(Cl)Cl>[CH2:27]([NH:29][C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:25]([CH:26]=1)[C:8]1[N:9]([C:18]3[CH:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[C:10](=[O:17])[C:11]3[C:16]([C:7]=1[N:6]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:31])[CH3:28]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 24771431HCID 24771431, compound

Product 1

HCID 24771485HCID 24771485, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of compound 53 (1.0 equiv., 0.276 mmol, 0.100 g) and ethyl isocyanate (5.0 equiv., 1.382 mmol, 0.098 g) in chloroform (3 ml) was stirred at room temperature for 9 days. The resulting precipitate was filtered off and successively washed with methanol, isopropanol and isopropyl ether to give 1-ethyl-3-[6-(6-chloro-pyridin-3-yl)-5,6-dihydro-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-9-yl]-urea (60) (0.046 g, yield=38%, purity (LC)=90%).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washsuccessively washed with methanol, isopropanol and isopropyl ether

Sources & evidence

ORD record
ord-1073950de04b42dcbf6632cc8e2f3739
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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