Dichloromethane methanol → (10S)-10-methyl-9,10-dihydro-8H-imidazo[1',2':1,2]imidazo[4,5-c]quinoline

HRID 415536Notes

Reaction equation

HRID 415536 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@@H:15]([CH3:25])[CH2:16][NH:17][C:18](=O)OC(C)(C)C)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.CO.C(Cl)Cl>C(#N)C>[CH3:25][C@@H:15]1[N:14]2[C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[N:6]=[CH:5][C:4]=3[N:1]=[C:18]2[NH:17][CH2:16]1

Participants

4

Reactant 2

HCID 21226129Dichloromethane methanolHCID 86624122tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate

Product 1

HCID 136174532(10S)-10-methyl-9,10-dihydro-8H-imidazo[1',2':1,2]imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from tert-butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate according to the methods of Parts C through G of Example 22 with the following modifications. Part C was carried out in acetonitrile as the solvent. Part D required chromatography (SiO2, 0-6% methanol/CH2Cl2). Following chromatographic purification (SiO2, 20-40% CMA/CHCl3) in Part G, the title compound, (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline (2.14 g), was obtained as an off white foam.

Workup

  1. custompurification (SiO2, 20-40% CMA/CHCl3) in Part G

Sources & evidence

ORD record
ord-1507ecaf1eeb45718b3de10a35e81565
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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