2,5-Dimethoxytetrahydrofuran → 1-(2-methylpropyl)-8-(1-pyrrolyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9473

Reaction equation

HRID 9473 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[N:17]=[C:16]([NH2:21])[C:15]3[N:22]=[CH:23][N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:14]=3[C:13]=2[CH:12]=1>C(O)(=O)C>[CH3:27][CH:26]([CH3:28])[CH2:25][N:24]1[C:14]2[C:13]3[CH:12]=[C:11]([N:10]4[CH:3]=[CH:7][CH:6]=[CH:5]4)[CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:21])[C:15]=2[N:22]=[CH:23]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 111961298-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219841381-(2-methylpropyl)-8-(1-pyrrolyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 57.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,5-Dimethoxytetrahydrofuran (1.6 mL of 95%, 12 mmol) was added to a suspension of 8-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 12 mmol) in acetic acid (60 mL), and the reaction was heated at reflux for one hour. The resulting dark brown solution was concentrated under reduced pressure, and the residue was mixed with water. The resulting mixture was made basic with the addition of ammonium hydroxide and stirred for 30 minutes. The resulting precipitate was isolated by filtration, washed with water, dried, and recrystallized from ethanol (100 mL). The crystals were collected in three crops. The first crop was dried for a day in a vacuum oven at 100° C. to provide 2.1 g of 1-(2-methylpropyl)-8-(1-pyrrolyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, mp 227.5–231.5° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for one hour
  3. concentrationThe resulting dark brown solution was concentrated under reduced pressure
  4. additionthe residue was mixed with water
  5. additionThe resulting mixture was made basic with the addition of ammonium hydroxide
  6. customThe resulting precipitate was isolated by filtration
  7. washwashed with water
  8. customdried
  9. customrecrystallized from ethanol (100 mL)
  10. customThe crystals were collected in three crops
  11. customThe first crop was dried for a day in a vacuum oven at 100° C.

Sources & evidence

ORD record
ord-bdb211b4df684f309f1596fd2503ee77
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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