Hydrochloric Acid → 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 81884Notes

Reaction equation

HRID 81884 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][CH2:27][O:28][CH3:29])[N:14]([CH2:15][CH2:16][CH2:17][NH:18]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.Cl>O1CCOCC1>[NH2:18][CH2:17][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]=[C:13]1[CH2:26][CH2:27][O:28][CH3:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10318754Tert-butyl 3-(4-amino-2-(2-methoxyethyl)-1h-imidazo[4,5-c]quinolin-1-yl)propylcarbamate

Product 1

HCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-Butyl 3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (5 g, U.S. Pat. No. 6,573,273, example 148) and hydrochloric acid in dioxane (100 mL of 4 M) were combined and stirred for 4 hours at ambient temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (30 mL). The pH was adjusted to pH 8 with 6 M sodium hydroxide. The solution was diluted with dichloromethane, ethyl acetate, triethylamine, and brine. The organic layer was concentrated under reduced pressure to provide an orange solid. This material was purified by prep HPLC (COMBIFLASH system eluting first with a gradient of 0 to 10% methanol in dichloromethane containing 1% ammonium hydroxide and then with a gradient of 9 to 30% methanol in dichloromethane containing 1% ammonium hydroxide) to provide 1.58 g of 1-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (30 mL)
  3. additionThe solution was diluted with dichloromethane, ethyl acetate, triethylamine, and brine
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customto provide an orange solid
  6. customThis material was purified by prep HPLC (COMBIFLASH system
  7. washeluting first with a gradient of 0 to 10% methanol in dichloromethane containing 1% ammonium hydroxide

Sources & evidence

ORD record
ord-21a5e11b2d44461f99acfde1a96cb6ac
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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