Calcium Chloride → (1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl)methyl acetate

HRID 1044313Notes

Reaction equation

HRID 1044313 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[N:26]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[C:27](=[O:31])[N:28]([CH2:29][CH3:30])[C:21]=12)(=[O:17])[CH3:16].CC(C)([O-])C.[K+].[Cl-].[Cl-].[Ca+2]>CC(N(C)C)=O>[C:15]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[N:26]([C:32]3[CH:33]=[CH:34][C:35]([O:38][C:3]4[N:2]([CH3:1])[C:6]5=[N:7][CH:8]=[CH:9][CH:10]=[C:5]5[N:4]=4)=[CH:36][CH:37]=3)[C:27](=[O:31])[N:28]([CH2:29][CH3:30])[C:21]=12)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 5284359Calcium ChlorideHCID 23665647Potassium tert-butoxideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 58577626[1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate

Product 1

HCID 58577346(1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl)methyl acetateYield 4.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (110 mg) was added to a solution of [1-ethyl-3-(4-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl]methyl acetate (170 mg) and potassium tert-butoxide (69.9 mg) in DMA (1 mL) at room temperature. The mixture was stirred at 100° C. under a dry atmosphere (CaCl2 tube) for 30 min. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane) to give (1-ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl)methyl acetate (10 mg) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-9e9cb799f5d2496c9ba4ff194dce25e4
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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