Phenyl isocyanate → HCID 59130460, compound

HRID 1992583Notes

Reaction equation

HRID 1992583 reaction equation
C(N(CC)CC)C.[C:8]1([N:14]=[C:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:35]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:28]=[C:27]([NH2:36])[C:26]=2[N:25]=[C:24]1[CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)(Cl)Cl>[NH2:36][C:27]1[C:26]2[N:25]=[C:24]([CH2:37][CH2:38][CH2:39][CH3:40])[N:23]([CH2:22][CH2:21][CH2:20][CH2:19][O:18][NH:17][C:15]([NH:14][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:16])[C:35]=2[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:28]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 68537588HCID 68537588, compound

Product 1

HCID 59130460HCID 59130460, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

Triethylamine (495 μL, 3.55 mmol) and phenyl isocyanate (316 mg, 1.65 mmol) were added to a mixture of 1-[4-(aminooxy)butyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (580 mg, 1.77 mmol) in chloroform (10 mL). The reaction was heated at 50° C. overnight and became homogeneous. The solution was diluted with 1 chloroform, washed with brine (2×), dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure to provide the crude product as an orange solid (700 mg). The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in ratios ranging from 100:0 to 95:5) to provide 90 mg of N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]-N′-phenylurea as a white solid.

Workup

  1. washwashed with brine (2×)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationconcentrated under reduced pressure
  6. customto provide the crude product as an orange solid (700 mg)
  7. customThe crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in ratios ranging from 100:0 to 95:5)

Sources & evidence

ORD record
ord-9914a0ef76fc40298806d96115a3e78c
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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