Trifluoroacetic acid → HCID 18783933, compound

HRID 1108638Notes

Reaction equation

HRID 1108638 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([Cl:26])[C:16]=2[N:15]=[CH:14]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([Cl:26])[C:16]=2[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18783939HCID 18783939, compound

Product 1

HCID 18783933HCID 18783933, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.10 g (0.267 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-4-chloro-1H-imidazo-[4,5-c]quinoline was dissolved in 6 ml of methylene chloride. 0.21 ml (2.67 mmol) of trifluoroacetic acid was added thereto and the mixture was concentrated under reduced pressure. 2 ml of a 1N sodium hydroxide aqueous solution and brine were added to the residue and the mixture was extracted five times with chloroform. The extract was dried (Na2SO4) and concentrated under reduced pressure. The residue was triturated with diethyl ether (containing a small amount of methylene chloride) and the precipitate thus formed was collected by filtration to obtain 45 mg (0.164 mmol) of 1-(4-aminobutyl)-4-chloro-1H-imidazo[4,5-c]quinoline (shown below) as pale orange powder. ##STR44## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3400, 2950, 1670, 1520, 1360.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. addition2 ml of a 1N sodium hydroxide aqueous solution and brine were added to the residue
  3. extractionthe mixture was extracted five times with chloroform
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether (
  7. additioncontaining a small amount of methylene chloride) and the precipitate
  8. customthus formed
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-47a0af90b87f412d91d555edb98bdd6c
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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