Benzoyl chloride → N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide

HRID 353805Notes

Reaction equation

HRID 353805 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[CH:7]1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[NH2:19][C:10]1[C:9]2[N:8]=[CH:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chloride2×HCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 9798928N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 7.8 mmol) in pyridine (1 L) was warmed to 60° C. to dissolve the starting material. The solution was cooled to about 30° C. and then benzoyl chloride (1.1 g, 7.8 mmol) diluted with pyridine (100 mL) was slowly added. After 1 hour analysis by high performance liquid chromatography (HPLC) indicated that some starting material remained. Additional benzoyl chloride (0.3 g) was added and the reaction was warmed to 50° C. overnight. The reaction mixture was concentrated under vacuum. The resulting residue was combined with chloroform (200 mL) and 1% sodium carbonate (200 mL). The organic layer was separated and then concentrated under vacuum. The resulting residue was combined with propyl acetate (30 mL) and heated on a steam bath to dissolve the residue. The solution was allowed to cool. The resulting precipitate was isolated by filtration to provide N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide as a solid, m.p. 210-212° C. Analysis: Calculated for C21H21N5O: % C, 70.18; % H, 5.89; % N, 19.48. Found: % C, 69.49; % H, 5.97; % N, 19.64. 1H NMR (500 MHz, DMSO-d6) δ 8.48 (t, J=6.0 Hz, 1H), 8.22 (s, 1H), 8.04 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.0 Hz, 1H),7.50 (t, J=8.0 Hz, 1H), 7.43 (m, 3H), 7.21 (t, J=8.0 Hz, 1H), 6.62 (broad s, 2H), 4.64 (t, J=7.0 Hz, 2H), 3.30 (q, J=6.0 Hz, 2H), 1.92 (quintet, J=7.0 Hz, 2H), 1.58 (quintet, J=7.0 Hz, 2H); MS (EI) m/e 359.1746 (359.1746 calcd for C21H21N5O).

Workup

  1. dissolutionto dissolve the starting material
  2. temperatureThe solution was cooled to about 30° C.
  3. additionwas slowly added
  4. temperaturethe reaction was warmed to 50° C. overnight
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. customThe organic layer was separated
  7. concentrationconcentrated under vacuum
  8. temperatureheated on a steam bath
  9. dissolutionto dissolve the residue
  10. temperatureto cool
  11. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-c4513f97eeab498cb3b2a415030fded4
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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