Diisopropylethylamine → N-benzyl-1-(1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

The following was added to sequentially to DMF (3 mL): 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylic acid (90 mg, 0.315 mmol), DIPEA (0.170 mL, 0.945 mmol), and HATU (144 mg, 0.378 mmol). This was allowed to stir for 30 min at rt, after which time the crude N-benzylpiperidine-4-carboxamide (˜70 mg, 0.315 mmol) was added. The reaction was stirred at rt for 17 h, at which time the reaction was diluted with 1:1 EtOAc:diethyl ether and washed with 10% aq. sodium carbonate (2×), dried over magnesium sulfate, and concentrated. The residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes) to afford the title compound as an oil. Yield: (77 mg, 0.153 mmol, 51%) 1H NMR (400 MHz, CDCl3) 7.59, 7.34-7.14, 7.03, 5.73, 5.57, 5.43-5.32, 4.76, 4.43, 3.77-3.64, 3.10, 2.80, 2.19-1.52

1. stirringThe reaction was stirred at rt for 17 h, at which time the reaction
2. washdiethyl ether and washed with 10% aq. sodium carbonate (2×)
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. customThe residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes)

ORDレコード

ord-3d24471df73c4188ab81f0d26204cecc

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08846684B2