Tetrahydrofuran → N-(2-methylcyclopentyl)-3-methoxy-4-(2-propynyloxy)benzamide

HRID 601983

Reaction equation

HRID 601983 reaction equation
C1COCC1.Cl.[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH2:13].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]#[CH:35])[C:26](Cl)=[O:27]>O>[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH:13][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]#[CH:35])=[C:23]([O:22][CH3:21])[CH:24]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 191014392-Methylcyclopentan-1-amine hydrochlorideHCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57445683N-(2-methylcyclopentyl)-3-methoxy-4-(2-propynyloxy)benzamideYield 36.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 20 ml of THF, 0.50 g of 2-methylcyclopentylamine hydrochloride and 1.0 g of triethylamine was added 0.50 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride. The mixture obtained was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 235 mg of N-(2-methylcyclopentyl)-3-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 18 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bf4ea1c1e584c7eb2436317bd392241
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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