m-Chloroperbenzoic acid → HCID 86611635, compound

HRID 2362540Notes

Reaction equation

HRID 2362540 reaction equation
[CH3:1][O:2][N:3]([CH3:27])[C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:23][CH2:24][CH3:25].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>>[CH3:1][O:2][N:3]([CH3:27])[C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:15]([O-:36])=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86611632HCID 86611632, compound

Product 1

HCID 86611635HCID 86611635, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate N-methoxy-N-methyl-6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide (4.01 g, 10.9 mmol) by reaction with m-CPBA (6.13 g) to provide N-methoxy-N-methyl-6-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanamide followed by reaction with p-toluenesulfonyl chloride (2.53 g, 13.3 mmol) and ammonium hydroxide solution (40 mL) to provide 6-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methoxy-N-methylhexanamide) as an off-white solid after recrystallization from a mixture of ethyl acetate and hexane, mp 134-135° C.

Sources & evidence

ORD record
ord-de5dc4a90db04fa2be619e640eea9777
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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