Calcium Chloride → HCID 58577654, compound

HRID 587466Notes

Reaction equation

HRID 587466 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:39]=[CH:38][C:21]([O:22][C:23]3[N:27]([CH2:28][C:29](OCC)=[O:30])[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:20][CH:19]=2)[C:10]1=[O:40])[CH3:8].[Cl-].[Cl-].[Ca+2]>C1COCC1>[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[CH:20][C:21]([O:22][C:23]3[N:27]([CH2:28][CH2:29][OH:30])[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:38][CH:39]=2)[C:10]1=[O:40])[CH3:8]

Participants

5

Reactant 3

HCID 5284359Calcium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58577597HCID 58577597, compound

Product 1

HCID 58577654HCID 58577654, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (33.2 mg) was added to a solution of ethyl {2-[4-(1-ethyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate (200 mg) in THF (4 mL) at 0° C. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 30 min. The mixture was quenched with EtOAc and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 10%-50% EtOAc in hexane) to give 1-ethyl-3-(4-{[1-(2-hydroxyethyl)-1H-benzimidazol-2-yl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) as colorless crystals.

Workup

  1. customThe mixture was quenched with EtOAc
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with 10%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-2ebbf03e3ddc4f84bab37a4771b3b288
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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