Ethyl Acetate → HCID 66814331, compound

HRID 1097578Notes

Reaction equation

HRID 1097578 reaction equation
[N:1]#[C:2][Br:3].[CH3:4][C:5]1[C:6]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:7]([NH2:19])[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]=1[CH3:11].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[BrH:3].[CH3:11][C:10]1[N:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[N:19]=[C:2]([NH2:1])[N:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:6]=2[C:5]=1[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10476Cyanogen Bromide2×HCID 516892Sodium BicarbonateHCID 66814249HCID 66814249, compound

Product 1

HCID 66814331HCID 66814331, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Cyanogen bromide (1.11 g, 10.5 mmol) was added to a solution of 5,6-dimethyl-N4-(2-methylpropyl)-2-phenoxypyridine-3,4-diamine (2.5 g, 8.8 mmol) in ethanol (50 mL), and the solution was heated overnight at 90° C. An analysis by LC/MS indicated the presence of starting material, and additional cyanogen bromide (100 mg) was added. The reaction was heated for one additional hour and allowed to cool to ambient temperature. Ethyl acetate and saturated aqueous sodium bicarbonate were added. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 2-5% methanol in dichloromethane) to provide 1.46 g of 6,7-dimethyl-1-(2-methylpropyl)-4-phenoxy-1H-imidazo[4,5-c]pyridin-2-amine hydrobromide as a white powder.

Workup

  1. additionwas added
  2. temperatureThe reaction was heated for one additional hour
  3. temperatureto cool to ambient temperature
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (eluting with 2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-97c797c9acfb4f49a49aebbab6a1ff12
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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