Cyclohexanecarbonyl chloride → HCID 10287007, compound

HRID 746589Notes

Reaction equation

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

Participants

Reactant 2

HCID 75938Cyclohexanecarbonyl chloride

HCID 22344446HCID 22344446, compound

Product 1

HCID 10287007HCID 10287007, compoundYield 46.8%

Procedure

Using the general method of Example 195 except that the acid chloride was added in a dropwise fashion, 1-(3-aminopropyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 7.83 mmol) was reacted with cyclohexanecarbonyl chloride (1.14 g, 7.83 mmol) to provide 1.34 g of N-[3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]cyclohexanecarboxamide as a white powder, m.p. 234.4-235.4° C. Analysis: Calculated for C21H27N5O: % C, 69.01; % H, 7.45; % N, 19.16; Found: % C, 68.70; % H, 7.39; % N, 19.24.

Sources & evidence

ORD record: ord-1c06b3690a63428f90d13ba3f3e9e5e0
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393859B2

Reaction notes

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