Ammonia → 4-amino-1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol

HRID 388596Notes

Reaction equation

HRID 388596 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 178461674HCID 178461674, compound

Product 1

HCID 1784616764-amino-1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

4-Chloro-1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol (4.0 g, 12 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. over two nights. The volatiles were removed under reduced pressure. The crude product was purified twice by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.2:3.8:96). The chromatographed product was washed with acetonitrile and diethyl ether several times and dried in a vacuum oven to provide 260 mg of 4-amino-1-[(1S)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-ol as an off-white solid, mp 292-295° C.

Workup

  1. customwhich was sealed
  2. customThe volatiles were removed under reduced pressure
  3. customThe crude product was purified twice by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide
  5. washThe chromatographed product was washed with acetonitrile and diethyl ether several times
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6073c7ed7ed94a51a0b6a24a127a2968
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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