Triethylamine → N-(2-methylcyclopentyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide

HRID 602002

Reaction equation

HRID 602002 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH2:8].C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:30][CH3:31])[C:25]=1[O:26][CH2:27][C:28]#[CH:29])[C:20](Cl)=[O:21]>C(OCC)(=O)C>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH:8][C:20](=[O:21])[C:19]1[CH:23]=[C:24]([O:30][CH3:31])[C:25]([O:26][CH2:27][C:28]#[CH:29])=[C:17]([F:16])[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 191014392-Methylcyclopentan-1-amine hydrochlorideHCID 574456983-Fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701166N-(2-methylcyclopentyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamideYield 69.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 1 ml of ethyl acetate and 0.2 g of 2-methylcyclopentylamine hydrochloride was added 0.48 ml of triethylamine and then, a mixture of 0.24 g of 3-fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride and 1 ml of ethyl acetate was added dropwise thereto under ice cooling. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to obtain 0.21 g of N-(2-methylcyclopentyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 70 of the present invention) represented by the formula:

Workup

  1. additionwas added dropwise
  2. customThe mixture obtained
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure
  4. customThe residue obtained

Sources & evidence

ORD record
ord-af8ac2f70c564e48a2e22ca7b8e5209f
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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