Triethylamine → 4-((6-phenoxypyridin-2-yl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666516
F[C:2](F)(F)[C:3](O)=O.N1CCC(=C[C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=2)[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)CC1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[CH:29]=1.C([N:46]([CH2:49][CH3:50])[CH2:47][CH3:48])C>CS(C)=O.O>[O:18]([C:19]1[N:20]=[C:21]([CH:2]=[C:3]2[CH2:48][CH2:47][N:46]([C:35]([NH:34][C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)=[O:43])[CH2:49][CH2:50]2)[CH:22]=[CH:23][CH:24]=1)[C:17]1[CH:16]=[CH:15][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66875752HCID 66875752, Verbindung

Produkt 1

HCID 249662004-((6-phenoxypyridin-2-yl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (127.97 mg, 0.480 mmol; Example 91, Step 2) in DMSO (2 mL) was added phenyl pyridin-3-ylcarbamate (102.88 mg, 0.480 mmol) and triethylamine (1.33 mL, 9.6 mmol). The resulting mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and concentrated. The crude compound was purified by silica gel column chromatography (30% acetone/hexane) to give the title compound (180 mg, 97% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.59 (s, 1H), 8.24-8.14 (m, 3H), 7.70 (t, J=7 Hz, 1H), 7.37 (m, 1H), 7.04-6.98 (m, 5H), 6.93 (d, J=8.5 Hz, 1H), 6.40 (s, 1H), 3.65 (t, J=5.5 Hz, 2H), 3.54 (t, J=5.5 Hz, 2H), 2.61 (t, J=5 Hz, 2H), 2.47 (t, J=5.5 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ ppm 163.64, 154.54, 154.13, 147.75, 140.67, 139.52, 138.86, 137.78, 129.47, 127.82, 125.20, 124.74, 121.46, 119.21, 118.62, 111.71, 45.72, 44.72, 35.76, 29.16; m/z (387.1 MH+); HPLC: 97.66%.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude compound was purified by silica gel column chromatography (30% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a6792474ecec46c791ba2acabcfd8072
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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