Water → HCID 10064416, compound

HRID 860159Notes

Reaction equation

HRID 860159 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:30][NH:31][CH3:32].O>CN(C)C=O>[CH3:30][N:31]([CH3:32])[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 10108376HCID 10108376, compound

Product 1

HCID 10064416HCID 10064416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Fluoro-5-[2-methyl-4-(2-methyl-pyridin-4-ylethynyl)-imidazol-1-yl]-pyridine (48) (100 mg, 0.34 mmol) was dissolved in 5 mL dimethyl formamide. Potassium carbonate (189 mg, 1.38 mmol) and dimethylamine hydrochloride (42 mg, 0.52 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was poured into 60 mL water and extracted three times with ethyl acetate (50 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient) and the desired compound was obtained as an off-white solid (22 mg, 20%), MS: m/e=318.2 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. extractionextracted three times with ethyl acetate (50 mL each)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0→90:10 gradient)

Sources & evidence

ORD record
ord-0fa48756870941f6bd0f2101177fffce
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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