Benzoyl chloride → HCID 23512658, compound

HRID 746575Notes

Reaction equation

HRID 746575 reaction equation
[NH2:1][CH2:2][C:3]([CH3:24])([CH3:23])[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][O:21][CH3:22].C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][O:21][CH3:22])[N:5]([CH2:4][C:3]([CH3:24])([CH3:23])[CH2:2][NH:1][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22344442HCID 22344442, compound

Product 1

HCID 23512658HCID 23512658, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 1-(3-amino-2,2-dimethylpropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 3.05 mmol) and triethylamine (470 μL, 3.36 mmol) in 1-methyl-2-pyrrolidinone (30 mL) was cooled to 0° C. Benzoyl chloride (345 μL, 3.05 mmol) was slowly added dropwise. The reaction mixture was allowed to slowly warm to ambient temperature overnight. The reaction mixture was combined with 1% aqueous sodium bicarbonate solution (150 mL) and then stirred overnight. A fine white precipitate was isolated by filtration and washed with hexanes. The material was dissolved in dichloromethane, methanol and toluene. The solution was concentrated under vacuum. The material was purified by column chromatography (60 g silica gel eluting with 7.5% methanol in dichloromethane) and then dried in a vacuum oven at 50° C. for 2 days to provide 0.82 g of N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl}benzamide as an off white powder, m.p. 103-125° C. Analysis: Calculated for C25H29N5O2.0.30H2O: % C, 68.72; % H, 6.83; % N, 16.03; Found: % C, 68.50; % H, 6.55; % N, 16.02.

Workup

  1. temperatureto slowly warm to ambient temperature overnight
  2. customA fine white precipitate was isolated by filtration
  3. washwashed with hexanes
  4. dissolutionThe material was dissolved in dichloromethane
  5. concentrationThe solution was concentrated under vacuum
  6. customThe material was purified by column chromatography (60 g silica gel eluting with 7.5% methanol in dichloromethane)
  7. customdried in a vacuum oven at 50° C. for 2 days

Sources & evidence

ORD record
ord-188d3f1000c747c3b98601878ea50b91
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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