[NH2:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[CH:8]1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[CH:8][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][NH:1][C:28](=[O:30])[CH3:29])[C:19]=2[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[N:12]=1To a solution of the 1-[4-(aminooxy)butyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine from Part C (200 mg, 0.73 mmol) and triethylamine (512 μL, 3.56 mmol) in pyridine (25 mL) was added acetyl chloride (57 μL, 0.80 mmol). The solution was stirred for 30 minutes at ambient temperature, and additional acetyl chloride (1 equivalent) was added. After 1 hour, water was added and the mixture was extracted with dichloromethane (2×). The aqueous layer was concentrated under reduced pressure to yield a white solid that was purified by chromatography (silica gel, gradient elution with 0-10% methanol in dichloromethane with a small amount of concentrated ammonium hydroxide added) to provide 30 mg of N-[4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]acetamide as a white solid.
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