Diisopropylethylamine → HCID 70665004, compound

HRID 1403549Notes

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.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>CS(C)=O.O>[C:33]([O:32][C:30]([N:27]1[CH2:28][CH2:29][CH:24]([NH:23][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)[CH2:25][CH2:26]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (300.0 mg, 0.95 mmol) in DMSO (2 mL) was added tert-butyl 4-aminopiperidine-1-carboxylate (227.0 mg, 1.14 mmol), DIEA (367.0 mg, 2.82 mmol). The resulting solution was stirred overnight at 100° C. and then diluted with water (10 mL), extracted with dichloromethane (3×10 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography with 20%-50% ethyl acetate in petroleum ether to afford methyl 3-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (200 mg, 44%).

Workup

extractionextracted with dichloromethane (3×10 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography with 20%-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-ab47aed22d9d4de18d1acd6eafb951cb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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