m-Chloroperbenzoic acid → HCID 68936722, compound

HRID 521291Notes

Reaction equation

HRID 521291 reaction equation
[C:1]1([C:7](=[O:35])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:31]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N:24]=[CH:23][C:22]=3[N:21]=[C:20]2[CH2:32][CH2:33][CH3:34])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:44])C=1>>[O-:44][N+:24]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=2[C:31]2[N:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:35])[C:20]([CH2:32][CH2:33][CH3:34])=[N:21][C:22]=2[CH:23]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69507055HCID 69507055, compound

Product 1

HCID 68936722HCID 68936722, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-phenyl-12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecan-1-one (6.0 g, 12.8 mmol) by reaction with m-CPBA (8.18 g) to provide 12-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenyldodecan-1-one followed by reaction with p-toluenesulfonyl chloride (3.65 g, 19.2 mmol) and ammonium hydroxide solution (40 mL). The product was dissolved a mixture of ethanol and diethyl ether, and a solution of hydrogen chloride (1 equivalent of a 1.0 M solution in diethyl ether) was added. A precipitate formed, and the solvents were removed under reduced pressure. The resulting solid was recrystallized from a mixture of isopropanol and hexane to provide 12-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenyldodecan-1-one hydrochloride as an off-white solid, mp 195-196° C.

Sources & evidence

ORD record
ord-3040e4cc234743e7b2d26428a73ba4c1
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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