Ammonia → 1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine

HRID 547321Notes

Reaction equation

HRID 547321 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:25])([O:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:26].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH3:17][C:16]([O:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])([CH3:25])[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]([NH2:26])[C:11]=2[N:12]=[CH:13]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 866134654-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

Product 1

HCID 589173181-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline (4.30 g, 11.3 mmol) in a solution of ammonia in methanol (7 M, 43 mL) in a high pressure vessel was heated at 150° C. for 12 hours. The vessel was allowed to cool to room temperature. The mixture was concentrated under reduced pressure to afford a solid that was slurried in water (50 mL), saturated aqueous sodium carbonate, and methanol. The solid was isolated by filtration, washed with water, and purified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane) to provide a white solid. The solid was heated in methanol (200 mL) at reflux, isolated by filtration, washed with methanol, and dried to yield 2.2 g of 1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 261-264° C.

Workup

  1. temperatureto cool to room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto afford a solid
  4. customThe solid was isolated by filtration
  5. washwashed with water
  6. custompurified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane)
  7. customto provide a white solid
  8. temperatureat reflux
  9. customisolated by filtration
  10. washwashed with methanol
  11. customdried

Sources & evidence

ORD record
ord-12db86334a154871b7df6ec0eff7b3fb
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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