Triethylamine → HCID 66814539, compound

HRID 1097576Notes

Reaction equation

HRID 1097576 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]=[C:11]=S)[CH3:9].[CH3:13][C:14]1[C:15]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:16]([NH2:28])[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:18][C:19]=1[CH3:20]>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:8]([NH:10][C:11]1[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:15]2[C:14]([CH3:13])=[C:19]([CH3:20])[N:18]=[C:17]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]=2[N:28]=1)[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10966Ethyl isothiocyanateHCID 66814249HCID 66814249, compound

Product 1

HCID 66814539HCID 66814539, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (2.44 mL, 17.5 mmol) and ethyl isothiocyanate (0.92 g, 10.5 mmol) were sequentially added to a solution of 5,6-dimethyl-N4-(2-methylpropyl)-2-phenoxypyridine-3,4-diamine (2.5 g, 8.8 mmol) in pyridine (25 mL), and the reaction was heated for five minutes at 80° C. 1,(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.63 g, 10.5 mmol) was added, and the reaction was heated at 100° C. for two hours, allowed to cool to ambient temperature, and diluted with ethyl acetate. The resulting solution was washed sequentially with brine (2×) and saturated aqueous sodium bicarbonate (1×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide an oil. The crude product was purified by column chromatography on silica gel (eluting with 1-3% methanol in dichloromethane) to provide 1.73 g of N-ethyl-6,7-dimethyl-1-(2-methylpropyl)-4-phenoxy-1H-imidazo[4,5-c]pyridin-2-amine as an oil which solidified to white crystals upon standing overnight at ambient temperature.

Workup

  1. temperaturethe reaction was heated at 100° C. for two hours
  2. temperatureto cool to ambient temperature
  3. washThe resulting solution was washed sequentially with brine (2×) and saturated aqueous sodium bicarbonate (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide an oil
  8. customThe crude product was purified by column chromatography on silica gel (eluting with 1-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-08b87fb59c8d4944bff78fa829241da7
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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