Cyclopentanecarbonyl chloride → HCID 58833703, compound

HRID 540848Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH3:28])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH2:18][CH2:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:26])[C:8]=2[N:27]=1)[CH2:2][CH2:3][CH3:4].[CH:29]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH2:1]([C:5]1[N:6]([CH3:28])[C:7]2[C:16]3[CH:15]=[C:14]([O:17][CH2:18][CH2:19][CH:20]4[CH2:21][CH2:22][N:23]([C:34]([CH:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)=[O:35])[CH2:24][CH2:25]4)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:26])[C:8]=2[N:27]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 78284Cyclopentanecarbonyl chloride

HCID 58833623HCID 58833623, compound

Product 1

HCID 58833703HCID 58833703, compound

Procedure

A modification of the method described in Example 15 was used to treat 2-butyl-1-methyl-8-(2-piperidin-4-ylethoxy)-1H-imidazo[4,5-c]quinolin-4-amine with cyclopentanecarbonyl chloride. The crude product was purified by column chromatography on silica gel to provide 2-butyl-8-{2-[1-(cyclopentylcarbonyl)piperidin-4-yl]ethoxy}-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 147.2-150.1° C.

Workup

customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-69462e7e387b4100bacedfa119059658
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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