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

HRID 1192890ノート

反応式

HRID 1192890 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-166f98389d724760a6cd5adebd7c7dc2
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

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