Hydrochloric Acid → HCID 67051022, compound

HRID 2383113Notes

Reaction equation

HRID 2383113 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:28][CH2:29][O:30][CH3:31])[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:11]=2[C:10]2[CH:9]=[CH:8][C:7]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:6][C:5]=2[N:4]=1.[OH-].[NH4+]>C(O)C.O>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:6][C:5]=3[N:4]=[C:3]([NH2:2])[C:12]=2[N:13]=[C:14]1[CH2:28][CH2:29][O:30][CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86626161HCID 86626161, compound

Product 1

HCID 67051022HCID 67051022, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of hydrochloric acid (9.25 mL of 2 M) in ethanol was added to tert-butyl {4-[4-amino-7-benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate (2 g, 4 mmol), and the reaction was heated at 70° C. for 5 hours. The reaction was allowed to cool to ambient temperature, and nitrogen gas was bubbled through the solution overnight. The solvent was removed under reduced pressure, and the residue was triturated with diethyl ether to provide a sticky solid, which was dissolved in water and treated with concentrated ammonium hydroxide until pH 11 was achieved. The solution was extracted with dichloromethane several times, and the combined extracts were concentrated under reduced pressure to provide 1-(4-aminobutyl)-7-benzyloxy-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a dark-brown oil.

Workup

  1. temperatureto cool to ambient temperature
  2. customnitrogen gas was bubbled through the solution overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was triturated with diethyl ether
  5. customto provide a sticky solid, which
  6. extractionThe solution was extracted with dichloromethane several times
  7. concentrationthe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-4afcdd5adb2840d8810bb41f3c27aa17
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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