Triethylamine → 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

HRID 606044Notes

Reaction equation

HRID 606044 reaction equation
[OH:1][N:2]=[C:3](Cl)[CH3:4].[Cl:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:23][O:24][CH2:25][CH3:26])[N:19]([CH2:20][C:21]#[CH:22])[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[C:16]2[N:17]=[C:18]([CH2:23][O:24][CH2:25][CH3:26])[N:19]([CH2:20][C:21]3[O:1][N:2]=[C:3]([CH3:4])[CH:22]=3)[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69633Ethanimidoyl chloride, N-hydroxy-HCID 862475854-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 866168734-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Hydroxyethanimidoyl chloride (prepared as described in Part D of Example 1, 2.10 g, 22.5 mmol) was added to a solution of 4-chloro-2-(ethoxymethyl)-1-prop-2-ynyl-1H-imidazo[4,5-c]quinoline prepared as described in Part D of Example 3, 5.39 g, 18.0 mmol) and triethylamine (3.70 mL, 27.0 mmol) in dichloromethane (60 mL). The solution was heated at reflux for 16 hours and then was concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution from 7:3 to 2:3 hexanes/ethyl acetate) to provide 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (4.21 g) as a white solid.

Workup

  1. customprepared
  2. temperatureThe solution was heated
  3. temperatureat reflux for 16 hours
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 7:3 to 2:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f7cf02884dfa45e38093690c331ec0a7
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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