[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21](OC)(OC)(OC)[CH3:22].CO.CCOC(C)=O>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH3:21][C:22]1[N:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1A solution of tert-butyl N′-(3-aminoquinolin-4-yl)hydrazinecarboxylate (11.67 g, 42.5 mmol) in 400 mL of anhydrous toluene was treated with trimethyl orthoacetate (5.96 mL, 46.8 mmol) and pyridine hydrochloride (100 mg) under an atmosphere of N2 and heated to reflux. After stirring for 3 h, the reaction mixture was concentrated under reduced pressure to give a red solid. Chromatography (SiO2, 0–10% MeOH/EtOAc) gave tert-butyl N-(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (10.7 g) as a yellow foam.
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