Hydrochloric Acid → HCID 58577354, compound

HRID 587500Notes

Reaction equation

HRID 587500 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]([CH3:13])[C:6]2[C:7]([N:12]=1)=[N:8][CH:9]=[CH:10][CH:11]=2.[CH2:14]([N:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[C:17]1=[O:32])[CH3:15].[Cl-].[Cl-].[Ca+2].Cl>CN(C=O)C>[CH2:14]([N:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:4]3[N:5]([CH3:13])[C:6]4[C:7]([N:12]=3)=[N:8][CH:9]=[CH:10][CH:11]=4)=[CH:29][CH:30]=2)[C:17]1=[O:32])[CH3:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 585772702-chloro-1-methyl-1H-imidazo[4,5-b]pyridineHCID 585777461-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577354HCID 58577354, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of sodium hydride (14.32 mg), 2-chloro-1-methyl-1H-imidazo[4,5-b]pyridine (100 mg) and 1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (152 mg) in DMF (3 mL) was stirred at 180° C. under a dry atmosphere (CaCl2 tube) for 20 min. The mixture was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give 1-ethyl-3-{4-[(1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (150 mg) as white crystals.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-6004f2f3f0b74a98b8c84901598ce893
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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