Tetrahydrofuran → N-cyclopentylmethyl-3,5-dimethoxy-(2-propynyloxy)benzamide

HRID 601988

Reaktionsgleichung

Reaktionsgleichung von HRID 601988
C1C[O:4][CH2:3]C1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:21][CH3:22])[C:16]=1OCC#C)[C:11](Cl)=[O:12].[CH:23]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(N([CH2:35][CH3:36])CC)C>C(OCC)(=O)C>[CH:23]1([CH2:28][NH:29][C:11](=[O:12])[C:10]2[CH:14]=[C:15]([O:21][CH3:22])[CH:16]=[C:8]([O:7][CH3:6])[C:9]=2[O:4][CH2:3][C:35]#[CH:36])[CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 80153CyclopentanemethylamineHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 86630486N-cyclopentylmethyl-3,5-dimethoxy-(2-propynyloxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5 ml of THF and 0.30 g of 3,5-dimethoxy-4-(2-propynyloxy)benzoyl chloride were added 0.15 g of 1-(cyclopentyl)methylamine and 0.21 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 0.13 g of N-cyclopentylmethyl-3,5-dimethoxy-(2-propynyloxy)benzamide (hereinafter, described as the compound 30 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-015122d8d0994657b0da4eacfc1f8910
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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