Ammonia → HCID 66814387, compound

HRID 1097596Notes

Reaction equation

HRID 1097596 reaction equation
[NH2:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6](Cl)[C:5]=2[N:15]=1.[NH3:28]>CO>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:3]1[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:28])[C:5]=2[N:15]=[C:2]1[NH2:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86626303HCID 86626303, compound

Product 1

HCID 66814387HCID 66814387, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

tert-Butyl 4-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)butylcarbamate (5.5 g, 14 mmol) and ammonia (50 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 170° C. for two days. The resulting solution was allowed to cool to room temperature and concentrated under reduced pressure. The resulting dark oil was partially dissolved in methanol, and diethyl ether was added. The mixture was stirred for one hour, and a solid was isolated by filtration. The solid was washed sequentially with diethyl ether and 90:10 dichloromethane:methanol (100 mL) and dried on the filter funnel for 30 minutes. The resulting green solid (2.52 g) was purified by automated flash chromatography on silica gel (eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 2.5:47.5:50) to provide 167 mg of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a dark green solid.

Workup

  1. customwhich was sealed
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting dark oil was partially dissolved in methanol
  5. additiondiethyl ether was added
  6. customa solid was isolated by filtration
  7. washThe solid was washed sequentially with diethyl ether and 90:10 dichloromethane
  8. dry with materialmethanol (100 mL) and dried on the filter funnel for 30 minutes
  9. customThe resulting green solid (2.52 g) was purified by automated flash chromatography on silica gel (
  10. washeluting with aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-d18651a85ca84fb984d600f9b8e0f33a
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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