Trifluoroacetic acid → HCID 22180889, compound

HRID 987195Notes

Reaction equation

HRID 987195 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:32][CH2:33][CH2:34][CH3:35])[N:21]([CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1>C(#N)C>[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:32][CH2:33][CH2:34][CH3:35])[N:21]([CH2:22][CH2:23][NH2:24])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22381765HCID 22381765, compound

Product 1

HCID 22180889HCID 22180889, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoroacetic acid (100 mL) was added with stirring to a solution of 1,1 -dimethylethyl N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (30.0 g, 78.2 mmol) in acetonitrile (100 mL). The reaction mixture was maintained at ambient temperature for 24 hours and then it was concentrated under vacuum. The residue was dissolved in a minimal amount of water and the pH of the solution was adjusted to pH 13 using 10% sodium hydroxide. The resulting precipitate was isolated by filtration and dried under high vacuum to provide 18.1 g of 2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethaneamine as an off-white solid, m.p. 196-199° C.

Workup

  1. concentrationit was concentrated under vacuum
  2. dissolutionThe residue was dissolved in a minimal amount of water
  3. customThe resulting precipitate was isolated by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-6c854083f7b44829965c801dd30ddeb8
Source dataset
uspto-grants-2003_10
Patent number
US06630588B2

Reaction notes

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