Ammonia → 2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606045Notes

Reaction equation

HRID 606045 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:22][O:23][CH2:24][CH3:25])[N:14]([CH2:15][C:16]3[O:20][N:19]=[C:18]([CH3:21])[CH:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:26]>CO>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:26])[C:11]=2[N:12]=1)[CH3:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866168734-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 590266862-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (4.21 g, 11.8 mmol) in a solution of 7 M ammonia in methanol (50 mL) was heated at 150° C. for 22 hours in a Parr pressure vessel. The volatiles were removed under reduced pressure and the resulting solid was triturated with water. A tan solid was isolated and purified by flash chromatography (silica gel, gradient elution from 9:1 to 1:1 chloroform/CMA) to yield 43.2 mg of pure 2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 178.0-180.0° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting solid was triturated with water
  3. customA tan solid was isolated
  4. custompurified by flash chromatography (silica gel, gradient elution from 9:1 to 1:1 chloroform/CMA)

Sources & evidence

ORD record
ord-b5685879c0d4441c93c32bfd5b0be417
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

Loading…