Sodium Hydroxide → HCID 18509836, compound

HRID 1370129Notes

Reaction equation

HRID 1370129 reaction equation
C([O:4][CH2:5][C:6]([N:9]1[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=[C:12]2[NH:11][C:10]1=[O:22])([CH3:8])[CH3:7])(=O)C.[H-].[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29]Br.[OH-].[Na+]>CN(C)C=O.CO.O1CCCC1>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29][N:11]1[C:12]2[C:13](=[N:14][CH:15]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:17]=2)[N:9]([C:6]([CH3:8])([CH3:7])[CH2:5][OH:4])[C:10]1=[O:22]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 114703704-(Bromomethyl)-2-chloro-1-methoxybenzeneHCID 18509897HCID 18509897, compound

Product 1

HCID 18509836HCID 18509836, compoundYield 79.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-acetoxy-1,1-dimethylethyl)-6-trifluoromethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (150 mg) in anhydrous N,N-dimethylformamide (1.5 mL) was added portionwise sodium hydride (20.8 mg, 60% dispersion in mineral oil) at 5° C. under nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. After adding 3-chloro-4-methoxybenzylbromide (117 mg), the mixture was stirred at room temperature for 4 hours. After adding tetrahydrofuran (2 mL), methanol (1 mL) and 1N-sodium hydroxide solution (1 mL), the mixture was refluxed for an hour. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The separated organic layer was washed successively with water, 1N-hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residual solid was washed with diethyl ether to give 1-(3-chloro-4-methoxybenzyl)-3-(1,1-dimethyl-2-hydroxyethyl)-6-trifluoromethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (161.6 mg) as an orange solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. temperaturethe mixture was refluxed for an hour
  3. temperatureAfter cooling to room temperature
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe separated organic layer was washed successively with water, 1N-hydrochloric acid
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated in vacuo
  9. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-7e1410c454ad40eaa4c76a0f8c6e98c5
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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