Azepane → Methyl 3-(azepan-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403391Notes

Reaction equation

Cl[C:2]1[C:3](=[O:16])[NH: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.[NH:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CS(C)=O>[N:26]1([C:2]2[C:3](=[O:16])[NH: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)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (500 mg, crude) in DMSO (6 mL) was added DIEA (543 mg, 4.20 mmol) and azepane (208 mg, 2.10 mmol). The solution was stirred overnight at 90° C. Then the reaction was quenched by the addition of water (50 mL), extracted with ethyl acetate (5×20 mL) and the organic layers were concentrated under vacuum to give a residue, which was purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether to afford methyl 3-(azepan-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (165 mg).

Workup

customThen the reaction was quenched by the addition of water (50 mL)
extractionextracted with ethyl acetate (5×20 mL)
concentrationthe organic layers were concentrated under vacuum
customto give a residue, which
customwas purified by a silica gel column with 1%-5% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-c06cebda1f1d45babd88ff6dc26fc991
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

Loading…