N-Methylisobutylamine → HCID 70664619, compound

HRID 1403643Notes

Reaction equation

Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[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.CCN(C(C)C)C(C)C.[CH2:32]([NH:36][CH3:37])[CH:33]([CH3:35])[CH3:34]>CS(C)=O.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([N:36]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH3:37])=[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:17][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (100 mg, 0.32 mmol) in DMSO (3 mL) was added DIEA (81.5 mg, 0.63 mmol) and isobutyl(methyl)amine (41 mg, 0.47 mmol), and the reaction was stirred overnight at 70° C. in an oil bath. The reaction mixture was cooled to room temperature, diluted with water (50 mL), and extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to give the residue, which was purified via silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 2-(4-fluorophenyl)-3-(isobutyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (80 mg, 69%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (3×20 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customto give the residue, which
customwas purified via silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-9f50d460183b4d49ac4bf8185cd35fef
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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