m-Chloroperbenzoic acid → HCID 68929891, compound

HRID 2362546Notes

Reaction equation

HRID 2362546 reaction equation
[CH3:1][C:2]([CH3:25])([CH2:18][C:19]1([CH3:24])[O:23][CH2:22][CH2:21][O:20]1)[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH3:17].C1C=C(Cl)C=C(C(OO)=[O:34])C=1>>[CH3:1][C:2]([CH3:25])([CH2:18][C:19]1([CH3:24])[O:23][CH2:22][CH2:21][O:20]1)[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-:34])=[CH:8][C:7]=2[N:6]=[C:5]1[CH3:17]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68928752HCID 68928752, compound

Product 1

HCID 68929891HCID 68929891, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate 1-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-2-methyl-1H-imidazo[4,5-c]quinoline (5.80 g, 17.1 mmol) by reaction with m-CPBA (7.5 g) to provide 1-[2,2-dimethyl-3-(2-methyl-[ 1,3]dioxolan-2-yl)propyl]-2-methyl-5-oxido-1H-imidazo[4,5-c]quinoline followed by reaction with p-toluenesulfonyl chloride (5.7 g, 30 mmol) and ammonium hydroxide solution (150 mL) to provide 1-[2,2-dimethyl-3-(2-methyl-[ 1,3]dioxolan-2-yl)propyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a light brown solid after recrystallization from a mixture of acetonitrile, methanol, and water, mp 209-211° C.

Sources & evidence

ORD record
ord-b15dce84a79d49d8a5ae4afa877c3c79
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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