Sodium Chloride → 1-[7-(Cyclohexylamino)-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-6-yl]ethanone

HRID 1506227Notes

Reaction equation

HRID 1506227 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[N:13][C:3]=12.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[Na+]>C(O)CO>[CH:22]1([NH:28][C:2]2[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][N:5]=[C:4]3[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[N:13][C:3]=23)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 7965CyclohexylamineHCID 712584351-(7-Chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-6-yl)ethanone

Product 1

HCID 712584381-[7-(Cyclohexylamino)-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-6-yl]ethanoneYield 83.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

1-[7-Chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-6-yl]ethanone (89.6 mg, 0.275 mmol) and cyclohexylamine (214 mg, 2.16 mmol) in ethylene glycol (2 mL) were stirred at 180° C. for 1 hour under microwave irradiation. The reaction mixture was allowed to cool to room temperature and, after addition of saturated aqueous sodium chloride, extracted with chloroform. The organic layer was stirred with 2 M hydrochloric acid (12 mL) at room temperature for 1 hour. The reaction mixture was basified with 10 M aqueous sodium hydroxide and extracted with chloroform, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a dark brown oil (88.9 mg, yield 83%).

Workup

  1. extractionextracted with chloroform
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-623c5092c40d4009afc251e754acfca9
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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