Trichloroacetyl isocyanate → HCID 57545309, compound

HRID 598378Notes

Reaction equation

HRID 598378 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-])=[CH:14][C:13]3[N:20]=[C:21]([CH2:36][O:37][CH2:38][CH3:39])[N:22]([CH2:23][C:24]([NH:27][C:28]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:29])([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:44]=C=O)=O>ClCCl>[NH2:44][C:14]1[C:13]2[N:20]=[C:21]([CH2:36][O:37][CH2:38][CH3:39])[N:22]([CH2:23][C:24]([NH:27][C:28]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:29])([CH3:25])[CH3:26])[C:12]=2[C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 67051010HCID 67051010, compound

Product 1

HCID 57545309HCID 57545309, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{2-[8-(benzyloxy)-2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide (2.41 g, 4.55 mmol) was suspended in dichloromethane (75 mL) and trichloroacetyl isocyanate (0.70 mL, 5.92 mmol) was added dropwise. After stirring for 1 hour, the volatiles were removed under reduced pressure. The resulting orange residue was dissolved in methanol (75 mL) and 6 mL of sodium methoxide (21% in methanol) was added. The reaction was stirred overnight and then the methanol was removed under reduced pressure. The residue was dissolved in dichloromethane and washed with water followed by brine. The organic fraction was dried over sodium sulfate, filtered and concentrated under reduced pressure to give an orange foam. The residue was purified by column chromatography on a HORIZON HPFC system. A silica gel cartridge was used eluting with a gradient of 10-20% CMA in chloroform to yield 1.51 g of N-{2-[4-amino-8-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide as a tan solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe resulting orange residue was dissolved in methanol (75 mL)
  3. addition6 mL of sodium methoxide (21% in methanol) was added
  4. stirringThe reaction was stirred overnight
  5. customthe methanol was removed under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialThe organic fraction was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give an orange foam
  12. customThe residue was purified by column chromatography on a HORIZON HPFC system
  13. washA silica gel cartridge was used eluting with a gradient of 10-20% CMA in chloroform

Sources & evidence

ORD record
ord-c0bd5ba88a754db3acb375320101506b
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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