Tetrahydrofuran → N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601986

Reaktionsgleichung

Reaktionsgleichung von HRID 601986
C1COCC1.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]#[CH:19])[C:10](Cl)=[O:11].[CH:20]1([CH2:26][NH2:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:20]1([CH2:26][NH:27][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]#[CH:19])=[C:7]([F:6])[CH:8]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 57445685N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamideAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 10 ml of THF and 0.40 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.45 g of cyclohexylmethylamine and 0.50 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.35 g of N-cyclohexylmethyl-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 22 of the present invention) represented by the formula:

Aufarbeitung

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7518b3286aba4f039c37a31571401569
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

Verknüpfte Notizen

Wird geladen…