Triethylamine → HCID 86626286, compound

HRID 1097566Notes

Reaction equation

HRID 1097566 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)[CH3:2].C(N=C=S)C.[NH2:13][C:14]1[C:15]([Cl:30])=[N:16][C:17]2[C:22]([C:23]=1[NH:24][CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])=[CH:21][CH:20]=[CH:19][CH:18]=2>N1C=CC=CC=1>[Cl:30][C:15]1[C:14]2[N:13]=[C:4]([NH:3][CH2:1][CH3:2])[N:24]([CH2:25][C:26]([CH3:27])([OH:28])[CH3:29])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10966Ethyl isothiocyanateHCID 226726541-((3-Amino-2-chloroquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 86626286HCID 86626286, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (3.15 mL, 22.6 mmol) and ethyl isothiocyanate (1.19 mL, 13.6 mmol) were sequentially added to a solution of 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol (3.00 g, 11.3 mmol) in pyridine (50 mL), and the reaction was heated for five minutes at 80° C. 1,(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.60 g, 13.6 mmol) was added slowly, and the reaction was heated overnight at 80° C., allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), and the resulting solution was washed with brine (3×) and water (1×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 2-3% methanol in dichloromethane) to provide 2.78 g of 1-[4-chloro-2-(ethylamino)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol.

Workup

  1. temperaturethe reaction was heated overnight at 80° C.
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. washthe resulting solution was washed with brine (3×) and water (1×)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (eluting with 2-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-cf738023575247548be573156e90ba76
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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