Ammonia → HCID 59026693, compound

HRID 606068Notes

Reaction equation

HRID 606068 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([CH2:15][CH2:16][N:17]3[C:21]([CH3:23])([CH3:22])[O:20][N:19]=[C:18]3[CH3:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:29]>CO>[CH2:27]([O:26][CH2:25][C:13]1[N:14]([CH2:15][CH2:16][N:17]2[C:21]([CH3:23])([CH3:22])[O:20][N:19]=[C:18]2[CH3:24])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:29])[C:11]=2[N:12]=1)[CH3:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86616885HCID 86616885, compound

Product 1

HCID 59026693HCID 59026693, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A slurry of 4-chloro-2-ethoxymethyl-1-[2-(3,5,5-trimethyl-1,2,4-oxadiazol-4(5H)-yl)ethyl]-1H-imidazo[4,5-c]quinoline (670 mg, 1.67 mmol) in a solution of 7 M ammonia in methanol (20 mL) was sealed in a pressure vessel and heated to 150° C. After 15 hours, the volatiles were removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 97:3 to 95:5 dichloromethane/methanol) to afford 2-ethoxymethyl-1-[2-(3,5,5-trimethyl-1,2,4-oxadiazol-4(5H)-yl)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (350 mg) as a white solid that was recrystallized from acetonitrile to give white needles, mp 204-205° C.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 97:3 to 95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-c874adb4c9124162aecfdaf7d05f11e7
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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