Cyclohexylamine → HCID 70665078, compound

HRID 1403560Notes

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.[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CS(C)=O.O>[CH:32]1([NH:38][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

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 (163.3 mg, 1.27 mmol) and cyclohexanamine (250.7 mg, 2.53 mmol), and the reaction was allowed to proceed with stirring overnight at 90° C. in an oil bath. The reaction mixture was cooled down to room temperature and diluted with water (150 mL). The mixture was extracted with ethyl acetate (3×80 mL), the organic layers combined and dried over magnesium sulfate, concentrated in vacuo to give the residue, which was purified by a silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford methyl 3-(cyclohexylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a light yellow solid (200 mg, 83%).

Workup

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

Sources & evidence

ORD record: ord-a6bac91bed0e452aa1e48b2ce56c2f8c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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