m-Chloroperbenzoic acid → HCID 86611637, compound

HRID 2362542Notes

Reaction equation

HRID 2362542 reaction equation
[CH3:1][O:2][N:3]([CH3:33])[C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:18]=[C:17]1[CH2:29][CH2:30][CH3:31].C1C=C(Cl)C=C(C(OO)=[O:42])C=1>>[CH3:1][O:2][N:3]([CH3:33])[C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]([O-:42])=[CH:20][C:19]=2[N:18]=[C:17]1[CH2:29][CH2:30][CH3:31]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86611633HCID 86611633, compound

Product 1

HCID 86611637HCID 86611637, compound

Procedure

The general methods described in Steps 9 and 10 of Example 1 and Step 7 of Example 16 was used to aminate N-methoxy-N-methyl-12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanamide (4.01 g, 8.86 mmol) by reaction with m-CPBA (6.13 g) to provide N-methoxy-N-methyl-12-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanamide followed by reaction with p-toluenesulfonyl chloride (2.53 g, 13.3 mmol) and ammonium hydroxide solution (40 mL) to provide 2-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methoxy-N-methyldodecanamide hydrochloride as an off-white solid after recrystallization of the hydrochloride salt from isopropanol, mp 156-158° C.

Sources & evidence

ORD record
ord-6ba99c90afb34491821622c9a630496d
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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