m-Chloroperbenzoic acid → HCID 69506961, compound

HRID 521308Notes

Reaction equation

HRID 521308 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:20][C:21]1([CH3:26])[O:25][CH2:24][CH2:23][O:22]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[CH2:17][CH2:18][CH3:19].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>>[CH3:27][C:2]([CH3:1])([CH2:20][C:21]1([CH3:26])[O:25][CH2:24][CH2:23][O:22]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-:36])=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68935391HCID 68935391, compound

Product 1

HCID 69506961HCID 69506961, 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-propyl-1H-imidazo[4,5-c]quinoline (3.10 g, 8.44 mmol) by reaction with m-CPBA (3.70 g) to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-5-oxido-2-propyl-1H-imidazo[4,5-c]quinoline followed by reaction with p-toluenesulfonyl chloride (2.80 g, 14.7 mmol) and ammonium hydroxide solution (100 mL) to provide 1-[2,2-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as off-white needles after recrystallization from aqueous methanol, mp 186-188° C.

Sources & evidence

ORD record
ord-ca6ac8bbfaff44689d9d7d4e63769142
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

Loading…