Water → HCID 178490887, compound

HRID 1370140Notes

Reaction equation

HRID 1370140 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]#[N:21])[CH:19]=[C:14]3[N:13]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([Cl:31])[CH:24]=3)[C:12]2=[O:32])[CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[Cl:31][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:29][CH3:30])[CH2:22][N:13]1[C:14]2[C:15](=[N:16][CH:17]=[C:18]([C:20]#[N: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:32]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium Carbonate3×HCID 178490890HCID 178490890, compound

Product 1

HCID 178490887HCID 178490887, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-(cis-4-acetoxycyclohexyl)-1-(3-chloro-4-methoxybenzyl)-6-cyano-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (150 mg) in methanol (3 ml) was added potassium carbonate (180 mg). The mixture was stirred at ambient temperature for 2 hours, then potassium carbonate (180 mg) was added thereto. After stirring for 2 hours, the mixture was added with potassium carbonate (180 mg). After stirring overnight, the mixture was added with water and extracted with chloroform. The extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a preparative thin-layer chromatography on silica gel developing with a mixture of ethyl acetate and n-hexane (2:1) to give 1-(3-chloro-4-methoxybenzyl)-6-cyano-3-(cis-4-hydroxycyclohexyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (50 mg) as an oil.

Workup

  1. stirringAfter stirring for 2 hours
  2. stirringAfter stirring overnight
  3. extractionextracted with chloroform
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by a preparative thin-layer chromatography on silica gel developing with a mixture of ethyl acetate and n-hexane (2:1)

Sources & evidence

ORD record
ord-14a1aeaa5f4d42d380a32ab9a84e91f8
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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