Diisopropylethylamine → HCID 70664906, compound

HRID 1403618Notes

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.[NH:23]1[CH2:28][CH:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CS(C)=O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([N:23]3[CH2:28][CH2:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[CH:25][CH2:24]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:17][CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (450 mg, 1.42 mmol) in DMSO (5.0 ml) was added 2-(1,2,3,6-tetrahydropyridin-4-yl)pyridine (300 mg, 1.87 mmol) and DIEA (361 mg, 2.79 mmol), and the reaction mixture was stirred overnight at 90° C. The reaction mixture was extracted with ethyl acetate (3×50 ml), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the residue, which was purified by preparative silica gel plate chromatography (dichloromethane:ethyl acetate:petroleum ether (40:1:12)) to afford methyl 2-(4-fluorophenyl)-3-(4-(pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)quinoxaline-6-carboxylate as a yellow solid (410 mg).

Workup

extractionThe reaction mixture was extracted with ethyl acetate (3×50 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give the residue, which
customwas purified by preparative silica gel plate chromatography (dichloromethane:ethyl acetate:petroleum ether (40:1:12))

Sources & evidence

ORD record: ord-dadf19edba4344e99b77b7b5edf4a823
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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