Ammonia → HCID 178508168, compound

HRID 388600Notes

Reaction equation

HRID 388600 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([OH:22])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:23]>CO>[NH2:23][C:2]1[C:11]2[N:12]=[C:13]([OH:22])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[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 178517324HCID 178517324, compound

Product 1

HCID 178508168HCID 178508168, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol (3.9 g, 12 mmol) and ammonia (70 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 150° C. overnight. The volatiles were removed under reduced pressure. The crude product was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.4:7.6:92). The chromatographed product was triturated twice with hot acetonitrile, collected by filtration, and dried in a vacuum oven to provide 800 mg of 4-amino-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol as a white solid, mp greater than 250° C.

Workup

  1. customwhich was sealed
  2. customThe volatiles were removed under reduced pressure
  3. customThe crude product was purified by automated flash chromatography (silica cartridge
  4. washeluting with aqueous ammonium hydroxide
  5. customThe chromatographed product was triturated twice with hot acetonitrile
  6. filtrationcollected by filtration
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-34f596f7246a4bdab8fd6e4efc15ba59
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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