3-Amino-1-propanol → 3-{[7-(Trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol

HRID 1893434Notes

Reaction equation

HRID 1893434 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:16]=[CH:17][N:18]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2.[NH2:19][CH2:20][CH2:21][CH2:22][OH:23]>O1CCOCC1.C(OCC)(=O)C>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]1[CH:16]=[CH:17][N:18]=[C:3]1[C:2]([NH:19][CH2:20][CH2:21][CH2:22][OH:23])=[N:11]2

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 593333224-Chloro-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline

Product 1

HCID 250700923-{[7-(Trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-olYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloro-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline (2.00 g; 7.36 mmol; 1 eq) in anhydrous dioxane (250 mL), 3-aminopropanol (6.2 mL; 81.0 mmol; 11 eq) is added, under argon atmosphere. Complete conversion was achieved after 17 hours of stirring under reflux. The initially cloudy yellow solution turns first orange and then becomes translucid. The reaction mixture is cooled to room temperature and diluted in ethyl acetate (500 mL). The organic phase is washed three times with a solution of saturated sodium hydrogenocarbonate (3×330 mL). The organic phases are combined, dried over sodium sulfate and concentrated under vacuum to provide pure title compound (1.94 g; 6.25 mmol; 85%) as a grey powder.

Workup

  1. temperatureunder reflux
  2. washThe organic phase is washed three times with a solution of saturated sodium hydrogenocarbonate (3×330 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08a51acf1cb145d2b872defd8ee11998
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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