Benzoyl chloride → HCID 23512658, compound

HRID 353890Notes

Reaction equation

HRID 353890 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

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 0C. 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 C25H29N5O2.0.30 H2O: % C, 68.72; % H, 6.83; % N, 16.03. Found: % C, 68.50; % H, 6.55; % N, 16.02.

Workup

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

Sources & evidence

ORD record
ord-4d1f47a870524a74a0d4f21c1651c166
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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