Ammonia → HCID 178461677, compound

HRID 388593Notes

Reaction equation

HRID 388593 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([OH:23])[N:14]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:24]>CO>[NH2:24][C:2]1[C:11]2[N:12]=[C:13]([OH:23])[N:14]([C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178461675HCID 178461675, compound

Product 1

HCID 178461677HCID 178461677, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

4-Chloro-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol (3.87 g, 11.9 mmol) and ammonia (65 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 135° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.2:4.8:95). The chromatographed product was triturated sequentially with hot acetonitrile, hot isopropanol, and hot ethanol and washed with diethyl ether after each trituration and filtration. The filtrates were combined, concentrated under reduced pressure, washed with diethyl ether, and dried in a vacuum oven overnight to provide 214 mg of 4-amino-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol as tan needles, mp greater than 250° C.

Workup

  1. customwhich was sealed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide
  5. customThe chromatographed product was triturated sequentially with hot acetonitrile, hot isopropanol, and hot ethanol
  6. washwashed with diethyl ether
  7. filtrationafter each trituration and filtration
  8. concentrationconcentrated under reduced pressure
  9. washwashed with diethyl ether
  10. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-2d3c695e298a4e63bd7ab1add12da252
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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