m-Chloroperbenzoic acid → HCID 68928218, compound

HRID 521287Notes

Reaction equation

HRID 521287 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=[O:33])C=1>>[O-:33][N+:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:6]2[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[C:4]([CH2:1][CH2:2][CH3:3])=[N:16][C:7]=2[CH:8]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68930143HCID 68930143, compound

Product 1

HCID 68928218HCID 68928218, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 7-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-2-one (5.0 g, 15.5 mmol) by reaction with m-CPBA (8.0 g) to provide 7-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-2-one followed by reaction with p-toluenesulfonyl chloride (4.42 g, 23.2 mmol) and ammonium hydroxide solution (50 mL) to provide 7-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)heptan-2-one) as an off-white solid after recrystallization from a mixture of acetonitrile, ethyl acetate, and hexane, mp 161-163° C.

Sources & evidence

ORD record
ord-6800870f023447d69691c6219c9f811b
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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