Acetone → HCID 57576725, compound

HRID 599409Notes

Reaction equation

HRID 599409 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][NH2:22])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:23][C:24]([CH3:26])=O>CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][N:22]=[C:24]([CH3:26])[CH3:23])[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[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 180AcetoneHCID 11370084HCID 11370084, compound

Product 1

HCID 57576725HCID 57576725, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (800 mg, 2.65 mmol) in acetone (10 mL) and methanol (10 mL) was stirred for 20 hours at room temperature, then was concentrated under reduced pressure. The resulting yellow solid was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 5-15% methanol in chloroform) followed by crystallization from acetonitrile to yield 400 mg of acetone O-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}oxime as pale yellow crystals, mp 212-216° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe resulting yellow solid was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 5-15% methanol in chloroform)
  3. customfollowed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-94793fc0804c4ec4ba922e4648ae503e
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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