Diisopropylethylamine → N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)benzo[d]isoxazole-3-carboxamide

HRID 623576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623576
Cl.[F:2][C:3]([F:16])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([C:35](Cl)=[O:36])=[N:27]1>ClCCl.C(OCC)(=O)C>[F:16][C:3]([F:2])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH:14][C:35]([C:28]2[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:26][N:27]=2)=[O:36])[CH3:13])=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 10419807Benzo[d]isoxazole-3-carbonyl ChlorideHCID 675094131-[6-(2,2,2-Trifluoroethoxy)-pyridin-3-yl]-ethylamine hydrochloride

Produkt 1

HCID 67511565N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)benzo[d]isoxazole-3-carboxamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (−)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (20 mg, 0.078 mmol, Amine-1, single enantiomer) and N,N-diisopropylethylamine (0.054 mL, 0.31 mmol) in dichloromethane (0.5 mL) is added dropwise a solution of benzo[d]isoxazole-3-carbonyl chloride (17 mg, 0.094 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction mixture is stirred at room temperature for 1 hour. The mixture is diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer is dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then preparative LC-MS to give 9.1 mg (32% yield) of the title compound.

Aufarbeitung

  1. washwashed with water (1.5 mL)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b296a370e2024324b87d64f57abd9c76
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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