Triethylamine → Ethyl 2-(1-methyl-4-(5-phenethylfuran-2-carboxamido)piperidin-4-yl)acetate

HRID 1192890노트

반응식

HRID 1192890 반응식
[NH2:1][C:2]1([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.CCN(CC)CC.[CH2:22]([C:30]1[O:34][C:33]([C:35](ON2C(=O)CCC2=O)=[O:36])=[CH:32][CH:31]=1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH3:8][N:5]1[CH2:4][CH2:3][C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([NH:1][C:35]([C:33]2[O:34][C:30]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:31][CH:32]=2)=[O:36])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 66865496Ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetateHCID 866498432,5-Dioxopyrrolidin-1-yl 5-phenethylfuran-2-carboxylate

생성물 1

HCID 66866225Ethyl 2-(1-methyl-4-(5-phenethylfuran-2-carboxamido)piperidin-4-yl)acetate수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred solution of ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate (16 mg, 0.077 mmol) in CH2Cl2 (1 mL) was treated with NEt3 (31 uL, 0.219 mmol), and 2,5-dioxopyrrolidin-1-yl 5-phenethylfuran-2-carboxylate, prepared as described in Preparation 5 (23 mg, 0.073 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the crude product purified by column chromatography to obtain the title compound (25 mg, 86%). 1H NMR (400 MHz, CD3OD) δ 7.29-7.16 (m, 5H), 7.00 (s, 1H), 6.17 (s, 1H), 4.06 (q, 2H, J=7.2 Hz), 3.05 (s, 4H), 2.88 (s, 2H), 2.75-2.69 (m, 2H), 2.54-2.48 (m, 2H), 2.41-2.31 (m, 5H), 1.87-1.81 (m, 2H), 1.15 (t, 3H, J=7.2 Hz); MS ESI 399.2 [M+H]+, calcd for [C23H30N2O4+H]+ 399.50.

후처리

  1. customprepared
  2. customthe solvent removed in vacuo
  3. customthe crude product purified by column chromatography

출처 및 근거

ORD 기록
ord-166f98389d724760a6cd5adebd7c7dc2
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680282B2

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