Hydrochloric Acid → 3-methyl-2-(2-(quinoxalin-2-yl)ethyl)-3H-imidazo[4,5-f]quinoline hydrochloride

HRID 868916Notes

Reaction equation

HRID 868916 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]1[NH:14][C:15]2[C:16]([N:25]=1)=[C:17]1[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[CH:18]1.[H-].[Na+].I[CH3:29].[ClH:30]>CN(C=O)C.CO>[ClH:30].[CH3:29][N:14]1[C:15]2[C:16](=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]=[CH:20][CH:19]=[CH:18]3)[N:25]=[C:13]1[CH2:12][CH2:11][C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 700988382-(2-(quinoxalin-2-yl)ethyl)-1H-imidazo[4,5-f]quinolineHCID 178419990HCID 178419990, compound

Product 1

HCID 701298313-methyl-2-(2-(quinoxalin-2-yl)ethyl)-3H-imidazo[4,5-f]quinoline hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(quinoxalin-2-yl)ethyl)-3H-imidazo[4,5-f]quinoline (100 mg, 0.31 mmol) or 2-(2-(quinoxalin-2-yl)ethyl)-1H-imidazo[4,5-f]quinoline (60 mg, 0.18 mmol) in DMF (3 mL or 2 mL, respectively) cooled in an ice bath was added sodium hydride (12 mg, 0.31 mmol; or 7 mg, 0.18 mmol; respectively). After stirring for 30 minutes, iodomethane (44 mg, 0.31 mmol; or 25 mg, 0.18 mmol; respectively) was added and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with water, washed with saturated sodium bicarbonate (10 mL), and extracted with DCM (20 mL×3). The combined organic layers were dried and concentrated to give a yellow solid as the free base. The free base may optionally be converted to a salt. For example, the free base was stirred in an HCl in methanol solution for 30 minutes to afford 3-methyl-2-(2-(quinoxalin-2-yl)ethyl)-3H-imidazo[4,5-f]quinoline hydrochloride (20 mg) or 1-methyl-2-(2-(quinoxalin-2-yl)ethyl)-M-imidazo[4,5-f]quinoline hydrochloride (25 mg) as a pale yellow solid.

Workup

  1. additionrespectively) was added
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe reaction was quenched with water
  4. washwashed with saturated sodium bicarbonate (10 mL)
  5. extractionextracted with DCM (20 mL×3)
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. customto give a yellow solid as the free base

Sources & evidence

ORD record
ord-435a48168fbc42548224d379820c2f68
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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