Triethylamine → 4-(3-methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666456
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:27]=1.C(N(CC)CC)C>CS(C)=O.O>[CH3:1][C:2]1[CH:18]=[C:17]([CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:8][N:7]=2)[CH:3]=1)[CH:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:33]([NH:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[O:34])[CH2:22][CH2:21]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668761222-(3-Methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

Produkt 1

HCID 668761034-(3-methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamideAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (445 mg, 1.276 mmol) in DMSO (3 mL) was added phenyl pyridin-3-ylcarbamate (273 mg, 1.276 mmol) followed by triethylamine (0.53 mL, 3.83 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% acetone-70% hexane) to give the pure title compound (0.350 g, 58% yield). 1H NMR (500 MHz, CDCl3): δ 8.45 (m, 2H), 8.27 (s, 1H), 8.01 (m, 1H), 7.90 (m, 1H), 7.02 (m, 1H), 6.92 (s, 1H), 6.84 (d, J=20 Hz, 2H), 6.47 (s, 1H), 6.38 (s, 1H), 3.16 (s, 2H), 3.52 (s, 2H), 2.61 (s, 2H), 2.47 (s, 2H), 2.37 (s, 3H); 13C NMR (125 MHz, CDCl3): δ 165.87, 154.81, 153.01, 145.50, 143.77, 141.29, 139.84, 138.79, 137.99, 136.71, 127.58, 126.93, 124.77, 123.58, 122.62, 121.62, 120.13, 118.82, 111.38, 45.72, 44.70, 35.78, 29.20, 21.45; m/z (469.5, M+H+); HPLC: 98.5%.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (30% acetone-70% hexane)

Quellen und Nachweise

ORD-Eintrag
ord-216abe6fe7504defbd821e3d654bf6a0
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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