Hydrochloric Acid → HCID 11601484, compound

HRID 1373984Notes

Reaction equation

HRID 1373984 reaction equation
C([O:3][CH2:4][C:5]1[N:6]([NH:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)C.B(Br)(Br)Br.Cl.[OH-].[Na+]>ClCCl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][OH:3])[N:6]([NH:19][CH:20]([CH3:22])[CH3:21])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10108777HCID 10108777, compound

Product 1

HCID 11601484HCID 11601484, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(ethoxymethyl)-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (prepared as described in Example 5, 0.502 g, 1.68 mmol) in dichloromethane (15 mL) under a nitrogen atmosphere was cooled in an ice bath. A solution of boron tribromide in dichloromethane (1 M, 4.19 mL, 4.19 mmol) was added dropwise. The mixture was allowed to warm slowly to room temperature, then was stirred for 16 hours. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure to yield a white solid. The solid was treated with 6 M aqueous hydrochloric acid (20 mL) to form a white suspension that was stirred at 50° C. for 2 hours. The mixture was allowed to cool to room temperature and was adjusted to pH 7 with 50% aqueous sodium hydroxide solution. A white solid was isolated by filtration, washed with water, and dried under vacuum. The crude product was purified by chromatography (silica gel, eluted with 1:1 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH)) then was recrystallized from acetonitrile to afford 0.0577 g of [4-amino-1-(isopropylamino)-1H-imidazo[4,5-c]quinolin-2-yl]methanol as white crystals, mp 228–229° C.;

Workup

  1. customThe reaction was quenched with methanol (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. customto yield a white solid
  4. customto form a white suspension that
  5. stirringwas stirred at 50° C. for 2 hours
  6. temperatureto cool to room temperature
  7. customA white solid was isolated by filtration
  8. washwashed with water
  9. customdried under vacuum
  10. customThe crude product was purified by chromatography (silica gel, eluted with 1:1 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH))
  11. customthen was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-e292831b4d9e43fc805f88f243df19e7
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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