Ammonia → HCID 178493987, compound

HRID 388619Notes

Reaction equation

HRID 388619 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([O:15][CH3:16])[NH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:17]>CO>[CH3:16][O:15][C:13]1[NH:14][C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:17])[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178493984HCID 178493984, compound

Product 1

HCID 178493987HCID 178493987, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-methoxy-1H-imidazo[4,5-c]quinoline (700 mg) was added to a high-pressure vessel with ammonia (40 mL of a 7 N solution in methanol), and the vessel was sealed and heated at 150° C. for 24 hours, allowed to cool, and concentrated under reduced pressure. The crude product was purified twice by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane first in a gradient from 0:0:100 to 0.3:4.7:95 and secondly in a gradient from 0:0:100 to 0.2:3.8:96) to provide 20 mg of 2-methoxy-1H-imidazo[4,5-c]quinolin-4-amine as a white solid. The compound was further purified by prep HPLC according to the method described in Examples 8-55. The observed accurate mass (M+H) for the isolated trifluoroacetate salt was 215.0931.

Workup

  1. customwas sealed
  2. temperatureto cool
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified twice by automated flash chromatography (silica cartridge
  5. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-cadbe2f103fb408a852a975a0180dbc4
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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