Acetonitrile → 1-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 746516Notes

Reaction equation

HRID 746516 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.FC(F)(F)C(O)=O.C(#N)C>O>[NH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 9883855Tert-butyl N-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate

Product 1

HCID 235127191-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 29.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyl N-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (14.8 g, 45.2 mmol), trifluoroacetic acid (100 mL) and acetonitrile (100 mL) were combined and maintained at ambient temperature overnight. The acetonitrile was removed and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was concentrated under vacuum to provide a tan solid. This material was dissolved in a minimal amount of hot water. The solution was adjusted to pH 14 and allowed to cool. The solution was concentrated under vacuum. The resulting residue was extracted with refluxing ethanol. The ethanol extract was concentrated under vacuum to provide 3.0 g of 1-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a tan solid, m.p. 265° C. 1H NMR (500 MHz, DMSO-d6) δ 8.14 (s, 1H), 8.08 (dd, J=8.0, 1.5 Hz, 1H), 7.62 (dd, J=8.0, 1.5 Hz, 1H), 7.44 (dt, J=8.0, 1.5 Hz, 1H), 7.25 (dt, J=8.0, 1.5 Hz, 1H), 6.58 (broad s, 2H), 4.54 (t, J=7.0 Hz, 2H), 3.01 (t, J=7.0 Hz, 2H), 1.60 (broad s, 2H); MS (EI) m/e 227.1171(227.1171 calcd for C12H13N5).

Workup

  1. customThe acetonitrile was removed
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2 hours
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. customto provide a tan solid
  6. temperatureto cool
  7. concentrationThe solution was concentrated under vacuum
  8. extractionThe resulting residue was extracted with refluxing ethanol
  9. extractionThe ethanol extract
  10. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-57a74cbaf7cf47d4b3e9289d96abc69c
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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