Sulfuric Acid → 2-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamide

HRID 1508872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508872
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]#[N:28])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1>C(=O)(O)[O-].[Na+]>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]([NH2:28])=[O:2])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 901111232-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile

Produkt 1

HCID 901093772-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Sulfuric acid (2 mL) was added to 2-(6-((2-(3-chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile (0.061 g, 0.18 mmol) at 0° C. and slowly warmed to rt. The mixture was stirred for 2 h, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.020 g, 34%) as a white solid. MW=368.22. 1H NMR (DMSO-d6, 300 MHz) δ 8.44-8.37 (m, 2H), 8.10-8.05 (m, 1H), 7.92 (s, 1H), 7.70-7.56 (m, 2H), 7.53-7.43 (m, 2H), 7.01 (s, 1H), 6.55 (d, J=9.4 Hz, 1H), 3.30 (d, 2H), 2.93 (q, J=7.6 Hz, 2H), 1.33 (t, J=7.6 Hz, 3H); APCI MS m/z 369 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b89de6c8223e48aa89f24b1e4a91e16a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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