4-Bromobenzoyl chloride → HCID 23512680, compound

HRID 746578Notes

Reaction equation

HRID 746578 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[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Br:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][C:30]([Br:29])=[CH:31][CH:32]=3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 22344439HCID 22344439, compound

Product 1

HCID 23512680HCID 23512680, compoundYield 60.6%

Procedure

Using the general method of Example 189, 1-(3-aminopropyl)-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin4-amine (2.0 g, 5.32 mmol) was reacted with 4-bromobenzoyl chloride (880 mg, 5.86 mmol) to provide 1.8 g of N-{3-[4-amino-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl} 4-bromobenzamide as a light yellow solid, m.p. 186.2-186.7° C. Analysis: Calculated for C29H28BrN5O2: % C, 62.37; % H, 5.05; % N, 12.54; Found: % C, 62.18; % H, 5.16; % N, 12.43.

Sources & evidence

ORD record
ord-9fc9cf560e234c0ab33ca2466ddde2e1
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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