Diisopropylethylamine → Methyl 2-phenyl-3-(4-(quinolin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

HRID 716912Notes

Reaction equation

HRID 716912 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.Cl.Cl.[N:24]1([C:30]2[N:31]=[CH:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>CN(C)C=O>[C:16]1([C:3]2[C:2]([N:27]3[CH2:26][CH2:25][N:24]([C:30]4[CH:39]=[CH:38][C:33]5[C:32](=[CH:37][CH:36]=[CH:35][CH:34]=5)[N:31]=4)[CH2:29][CH2:28]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 214769514-Isoquinolin-3-yl-piperazine dihydrochlorideHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67042108Methyl 2-phenyl-3-(4-(quinolin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Into a 8-mL sealed tube, was placed methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (150 mg, 0.44 mmol, 1.00 equiv), 3-(piperazin-1-yl)isoquinoline dihydrochloride (250.8 mg, 0.88 mmol, 2.00 equiv), DIEA (170.3 mg, 1.32 mmol, 3.00 equiv), N,N-dimethylformamide (3 mL). The resulting solution was 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 4×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 216.6 mg (crude) of methyl 3-(4-(isoquinolin-3-yl)piperazin-1-yl)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 8-mL sealed tube
  2. customThe reaction was then quenched by the addition of water
  3. extractionThe resulting solution was extracted with 4×30 mL of dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe mixture was concentrated under vacuum
  7. customThis resulted in 216.6 mg (crude) of methyl 3-(4-(isoquinolin-3-yl)piperazin-1-yl)-2-phenylquinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-0c7518f1424c484a89fee734921f8b1b
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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