Benzoyl chloride → HCID 23512661, compound

HRID 746571Notes

Reaction equation

HRID 746571 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]=[C:11]1[CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl>[NH2:23][C:14]1[C:13]2[N:12]=[C:11]([CH2:24][CH2:25][CH2:26][CH3:27])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 223444481-(8-Aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 23512661HCID 23512661, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(8-aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 3.26 mmol) and triethylamine (500 μL, 3.59 mmol) in dichloromethane (30 mL) was cooled to 0° C. Benzoyl chloride (380 μL, 3.26 mmol) was slowly added dropwise. The reaction mixture was allowed to slowly warm to ambient temperature. After several hours the reaction mixture was washed with distilled water (1×50 mL) and brine (2×50 mL), dried over sodium sulfate and then concentrated under reduced pressure to provide 1.5 g of crude orange gooey material. This material was purified by column chromatography (65 g of silica gel, eluting with 7.5% methanol in dichloromethane). The purified material was dissolved in a small amount of dichloromethane and the solution was diluted with hexane to precipitate a white powder. This material was isolated by filtration, washed with hexanes and then dried in a vacuum oven at 60° C. overnight to provide 0.72 g of N-[8-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)octyl]benzamide as a white powder, m.p. 149.5-151.3° C. Analysis: Calculated for C29H37N5O: % C, 73.85; % H, 7.91; % N, 14.85;

Workup

  1. washAfter several hours the reaction mixture was washed with distilled water (1×50 mL) and brine (2×50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto provide 1.5 g of crude orange gooey material
  5. customThis material was purified by column chromatography (65 g of silica gel, eluting with 7.5% methanol in dichloromethane)
  6. dissolutionThe purified material was dissolved in a small amount of dichloromethane
  7. additionthe solution was diluted with hexane
  8. customto precipitate a white powder
  9. customThis material was isolated by filtration
  10. washwashed with hexanes
  11. customdried in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-a4224cb40b1f4bdd9202e3dbca7b363e
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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