Trichloroacetyl isocyanate → HCID 57545281, compound

HRID 2383203Notes

Reaction equation

HRID 2383203 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]([CH2:32][O:33][CH2:34][CH3:35])[N:22]([CH2:23][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[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:40]=C=O)=O>ClCCl>[NH2:40][C:14]1[C:13]2[N:20]=[C:21]([CH2:32][O:33][CH2:34][CH3:35])[N:22]([CH2:23][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])([CH3:26])[CH3:25])[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 67051076HCID 67051076, compound

Product 1

HCID 57545281HCID 57545281, compoundYield 82.3%

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]methanesulfonamide (2.29 g, 4.59 mmol) was suspended in dichloromethane (75 mL) and trichloroacetyl isocyanate (0.71 mL, 5.97 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 for two additional hours 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 10-30% CMA in chloroform to provide 1.88 g of N-[2-(4-amino-8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a white powder, mp 90° C.

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 for two additional hours
  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 10-30% CMA in chloroform

Sources & evidence

ORD record
ord-864670e9382a4c5db4581d13030bf0c2
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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