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

HRID 1405288노트

반응식

HRID 1405288 반응식
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

참가 물질

5

반응물 3

HCID 8119AzepaneHCID 81531DiisopropylethylamineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

생성물 1

HCID 70654318Methyl 3-(azepan-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate수율 26.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-452322a3c27246768ed3cd93d275ec77
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916561B2

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