Diisopropylethylamine → HCID 67041935, compound

HRID 716866Notes

Reaction equation

HRID 716866 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:16]1([C:3]2[C:2]([N:33]3[CH2:32][CH2:31][N:30]([C:27]4[CH:26]=[CH:25][C:24]([C:23]([F:36])([F:37])[F:22])=[CH:29][CH:28]=4)[CH2:35][CH2:34]3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1217181-(4-(Trifluoromethyl)phenyl)piperazineHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67041935HCID 67041935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (150 mg, 0.44 mmol, 1.00 equiv) in DMF (8 mL), 1-(4-(trifluoromethyl)phenyl)piperazine (202 mg, 0.88 mmol, 2.00 equiv), DIEA (170.3 mg, 1.32 mmol, 3.00 equiv) were placed in a 20-mL sealed tube and stirred overnight at 100° C. in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 4×50 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate followed by filtration to remove solids. The resulting mixture was concentrated under vacuum, resulting in 177.4 mg (78%) of methyl 2-phenyl-3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customsealed tube
  2. customThe reaction was then quenched by the addition of water
  3. extractionThe resulting solution was extracted with 4×50 mL of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfollowed by filtration
  6. customto remove solids
  7. concentrationThe resulting mixture was concentrated under vacuum
  8. customresulting in 177.4 mg (78%) of methyl 2-phenyl-3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)quinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-4ab617af721e46fa89e43a28fc034f5e
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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