Ammonia → HCID 58917329, compound

HRID 547304Notes

Reaction equation

HRID 547304 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH3:26])[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.[NH3:27]>CO.O>[CH3:26][C:13]1[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]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:27])[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86613464HCID 86613464, compound

Product 1

HCID 58917329HCID 58917329, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 4-chloro-2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline (1.80 g, 4.55 mmol) in a solution of ammonia in methanol (7 M, 18 mL) in a high pressure vessel was heated at 150° C. for 14 hours. The vessel was allowed to cool to room temperature. A solid was isolated by filtration, washed with methanol, and purified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane) to provide a white solid. The solid was stirred in water (100 mL) for 1 hour, isolated by filtration, washed with water, and dried to yield 0.84 g of 2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 253-255° C.

Workup

  1. temperatureto cool to room temperature
  2. customA solid was isolated by filtration
  3. washwashed with methanol
  4. custompurified by flash chromatography (silica gel, eluted with 10% methanol in dichloromethane)
  5. customto provide a white solid
  6. customisolated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b03ed12e5da04f2d8fa3432f1ef8e9d9
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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