Hydrochloric Acid → HCID 58577344, compound

HRID 587505Notes

Reaction equation

HRID 587505 reaction equation
Cl[C:2]1[N:10]([CH3:11])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1.[CH2:12]([N:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:15]1=[O:30])[CH3:13].[H-].[Na+].[Cl-].[Cl-].[Ca+2].Cl>CN(C=O)C>[CH2:12]([N:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C:23]2[CH:24]=[CH:25][C:26]([O:29][C:2]3[N:10]([CH3:11])[C:5]4=[N:6][CH:7]=[CH:8][CH:9]=[C:4]4[N:3]=3)=[CH:27][CH:28]=2)[C:15]1=[O:30])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 108209862-Chloro-3-methyl-3H-imidazo[4,5-b]pyridineHCID 585777461-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577344HCID 58577344, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3-methyl-3H-imidazo[4,5-b]pyridine (150 mg) was added to a solution of 1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (228 mg) and NaH (39.4 mg) in DMF (2 mL) at 100° C. The mixture was stirred at 180° C. under a dry atmosphere (CaCl2 tube) for 1 h. 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 (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}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (200 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 (NH silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-6c0fbd4f6ea5450e946ddc0ed67c0e07
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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