Calcium Chloride → HCID 58577258, compound

HRID 1429922Notes

Reaction equation

HRID 1429922 reaction equation
BrC[Mg].[CH2:4]([N:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:36]=[CH:35][C:18]([O:19][C:20]3[N:24]([CH2:25]C(OCC)=O)[C:23]4[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=4[N:21]=3)=[CH:17][CH:16]=2)[C:7]1=[O:37])[CH3:5].[Cl-].[Cl-].[Ca+2]>C1COCC1>[CH2:4]([N:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:16]=[CH:17][C:18]([O:19][C:20]3[N:24]([CH2:25][C:18]([OH:19])([CH3:35])[CH3:17])[C:23]4[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=4[N:21]=3)=[CH:35][CH:36]=2)[C:7]1=[O:37])[CH3:5]

Participants

5

Reactant 3

HCID 5284359Calcium ChlorideHCID 58577597HCID 58577597, compoundHCID 178507037HCID 178507037, compound

Product 1

HCID 58577258HCID 58577258, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromomethylmagnesium (3M in ether, 1.924 mL) 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 (220 mg) in THF (40 mL) at 0° C. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 3 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give 1-ethyl-3-(4-{[1-(2-hydroxy-2-methylpropyl)-1H-benzimidazol-2-yl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (130 mg) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-bf99c045620a46ca8961691b1bd0a913
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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