Water → HCID 24771592, compound

HRID 1670711Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:27]([CH:28]=1)[C:8]1[N:9]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=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.[C:29]([O:32][CH2:33][CH2:34]Br)(=[O:31])[CH3:30].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:9]2[C:8]3[N:27]4[CH:28]=[C:2]([O:1][CH2:34][CH2:33][O:32][C:29](=[O:31])[CH3:30])[CH:3]=[CH:4][C:5]4=[N:6][C:7]=3[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:17])=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of compound 10 (1.0 equiv., 0.806 mmol, 0.300 g), 2-bromoethyl acetate (2.0 equiv., 1.611 mmol, 0.269 g) and K2CO3 (3.0 equiv., 2.417 mmol, 0.334 g) in dry DMF (5 ml) was stirred at 60° C. for 4 h. Water was added to the reaction mixture and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried with MgSO4 and concentrated in vacuo. Purification by column chromatography (dichloromethane/methanol 97.2:2.5) afforded 6-(4-nitrophenyl)-9-[2-[(1-oxoethyl)oxy]-ethoxy]-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (73) (0.245 g, yield=66%, purity (LC)=97%).

Workup

extractionthe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic layers were dried with MgSO4
concentrationconcentrated in vacuo
customPurification by column chromatography (dichloromethane/methanol 97.2:2.5)

Sources & evidence

ORD record: ord-b6a86b51f25b4c5e8117b42866ad7778
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994187B2

Reaction notes

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