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

HRID 1192892Notes

Reaction equation

HRID 1192892 reaction equation
[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.[C:22]1([C:28]#[C:29][C:30]2[O:34][C:33]([C:35](ON3C(=O)CCC3=O)=[O:36])=[CH:32][CH:31]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:31][CH:32]=2)=[O:36])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 574408102,5-Dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylateHCID 66865496Ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate

Product 1

HCID 66864746Ethyl 2-(1-methyl-4-(5-(phenylethynyl)furan-2-carboxamido)piperidin-4-yl)acetateYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of ethyl 2-(4-amino-1-methylpiperidin-4-yl)acetate (53 mg, 0.263 mmol) in CH2Cl2 (2 mL) was treated with NEt3 (0.11 mL, 0.789 mmol), and 2,5-dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylate, prepared as described in Preparation 5 (89 mg, 0.289 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the product purified by column chromatography to obtain the title compound (51 mg, 49%). 1H NMR (400 MHz, CD3OD) δ 7.57-7.53 (m, 2H), 7.44-7.40 (m, 3H), 7.16 (s, 1H), 6.84 (s, 1H), 4.08 (q, 2H, J=7.2 Hz), 2.89 (s, 2H), 2.70-2.65 (m, 2H), 2.54-2.47 (m, 2H), 2.39-2.25 (m, 5H), 1.85-1.80 (m, 2H), 1.17 (t, 3H, J=7.2 Hz); MS ESI 395.2 [M+H]+, calcd for [C23H26N2O4+H]+ 395.47.

Workup

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

Sources & evidence

ORD record
ord-30e4e0996ce64e21b4c4d37a5eb5eace
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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