Tert-Butylamine → HCID 70664982, compound

HRID 1403558Notes

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.[CH3:32][C:33]([NH2:36])([CH3:35])[CH3:34]>CS(C)=O.O>[C:33]([NH:36][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)([CH3:35])([CH3:34])[CH3:32]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.63 mmol) in DMSO (10 mL) was added DIEA (163 mg, 1.26 mmol) and 2-methylpropan-2-amine (461.3 mg, 6.32 mmol) with stirring overnight at 90° C. in an oil bath. The reaction mixture was cooled to room temperature, diluted with H2O (150 mL), extracted with ethyl acetate (3×80 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to give the residue, which was purified by silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 3-(tert-butylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a light yellow solid (115 mg, 51%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate (3×80 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customto give the residue, which
customwas purified by silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-8cd9658c0d0044968c27cfa34db4b0eb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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