Benzoyl chloride → HCID 23512730, compound

HRID 746576Notes

Reaction equation

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

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 223444381-(8-Aminooctyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 23512730HCID 23512730, compoundYield 28.1%

Procedure

Using the general method of Example 186 1-(8-aminooctyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.85 mmol) was reacted with benzoyl choride (450 μL, 3.85 mmol) to provide 0.45 g of N-[8-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)octyl]benzamide as an off white powder, m.p. 133.1-136.7° C. Analysis: Calculated for C25H29N5O.0.25H2O: % C, 71.49; % H, 7.08; % N, 16.67; Found: % C, 71.37; % H, 7.05; % N, 16.62.

Sources & evidence

ORD record: ord-dd7836cc675546838b0a65236e644b35
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393859B2

Reaction notes

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