HCID 9798742, compound → 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1108647Notes

Reaction equation

HRID 1108647 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]([NH2:26])[C:16]=2[N:15]=[CH:14]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[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]([NH2:26])[C:16]=2[N:15]=[CH:14]1

Participants

3

Reactant 1

HCID 9798742HCID 9798742, compound

Product 1

HCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 83.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

One hundred ml of trifluoroacetic acid was added to 16.04 g (45.13 mmol) 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]-quinoline-4-amine and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated to dryness. A 2N sodium hydroxide solution aqueous solution (120 ml) was added thereto and the mixture was stirred. The precipitate thus formed was collected by filtration and washed with water and diethyl ether to obtain 9.64 g (37.76 mmol) of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinoline-4-amine shown below as a pale yellowish white solid. ##STR56## Its physicochemical properties were in agreement with those of the compound of Example 17.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionA 2N sodium hydroxide solution aqueous solution (120 ml) was added
  3. stirringthe mixture was stirred
  4. customThe precipitate thus formed
  5. filtrationwas collected by filtration
  6. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-4ec1b28407a047f0a180e3fb028d8af7
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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