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

HRID 601988

Reaction equation

HRID 601988 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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:

Workup

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

Sources & evidence

ORD record
ord-015122d8d0994657b0da4eacfc1f8910
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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