m-Chloroperbenzoic acid → HCID 86611636, compound

HRID 521300Notes

Reaction equation

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

Participants

Reactant 2

HCID 70297m-Chloroperbenzoic acid

HCID 86611634HCID 86611634, compound

Product 1

HCID 86611636HCID 86611636, compound

Procedure

The general method described in Steps 9 and 10 of Example 1 was used to aminate N-methoxy-N-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyramide (7.4 g, 21.7 mmol) by reaction with m-CPBA (9.50 g) to provide N-methoxy-N-methyl-4-(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyramide followed by reaction with p-toluenesulfonyl chloride (7.20 g, 37.8 mmol) and ammonium hydroxide solution (200 mL) to provide 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-N-methoxy-N-methyl-butyramide as white crystals after recrystallization from aqueous methanol, mp 163-165° C.

Sources & evidence

ORD record: ord-c362346963fb43b99097b39ee4f6874c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328110B2

Reaction notes

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