Methanol → HCID 178490886, compound

HRID 1370137Notes

Reaction equation

HRID 1370137 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:15]3=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=[C:14]3[N:13]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)[C:12]2=[O:35])[CH2:7][CH2:6]1)(=O)C.CO.[OH-].[Na+]>O1CCCC1>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[CH2:24][N:13]1[C:14]2[C:15](=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=2)[N:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([OH:4])[CH2:10][CH2:9]2)[C:12]1=[O:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178490889HCID 178490889, compound

Product 1

HCID 178490886HCID 178490886, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(trans-4-acetoxycyclohexyl)-1-(3,4-dimethoxybenzyl)-6-trifluoromethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (125 mg) in a mixture of tetrahydrofuran (1 mL), methanol (0.5 mL) and 1N-sodium hydroxide (0.507 mL) was refluxed for an hour. After cooling to room temperature, the mixture was concentrated in vacuo. Water was added to the residue, and the resulting precipitate was collected by filtration. The obtained solid was washed with water and subjected to a preparative silica gel column chromatography eluting with 5% methanol in chloroform. The obtained solid was washed with a mixture of diethyl ether and diisopropyl ether to give 1-(3,4-dimethoxybenzyl)-3-(trans-4-hydroxycyclohexyl)-6-trifluoromethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (62.9 mg) as a colorless solid.

Workup

  1. temperaturewas refluxed for an hour
  2. concentrationthe mixture was concentrated in vacuo
  3. additionWater was added to the residue
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe obtained solid was washed with water
  6. washeluting with 5% methanol in chloroform
  7. washThe obtained solid was washed with a mixture of diethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-529dcd81cd6f4747b03fa45dd17c04b2
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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