Tetrahydrofuran → 2-[(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamide

HRID 2105501Notes

Reaction equation

[CH2:1]([C:4]1[N:5]([O:17][CH2:18][C:19]([NH2:21])=[O:20])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:27].C1COCC1>ClCCl>[O-:27][N+:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:6]2[N:5]([O:17][CH2:18][C:19]([NH2:21])=[O:20])[C:4]([CH2:1][CH2:2][CH3:3])=[N:16][C:7]=2[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamide (2.7 g, 9.5 mmol) in dichloromethane (100 mL) was cooled to approximately 0° C., and 3-chloroperoxybenzoic acid (3.2 g of approximately 77% pure material, 14 mmol) was added. The reaction was stirred for ten minutes at 0° C. and for one hour at room temperature. An analysis by LC/MS indicated that no reaction had occurred; the starting material was very insoluble. THF (40 mL) was added, and the reaction was stirred for 23 hours. An analysis by LC/MS indicated the presence of starting material, and dichloromethane (500 mL) was added. The reaction was stirred for seven hours, was allowed to stand for three days, and then was concentrated under reduced pressure to provide 2-[(5-oxido-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)oxy]acetamide.

Workup

stirringthe reaction was stirred for 23 hours
additionwas added
stirringThe reaction was stirred for seven hours
waitto stand for three days
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-b7d49c4d245f44c291a2379b7f5e2a02
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579359B2

Reaction notes

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