Ethyl Acetate → N-(2-methylcyclohexyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide

HRID 601996Notes

Reaction equation

HRID 601996 reaction equation
C(OCC)(=O)C.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:21][CH3:22])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH2:30]>C(N(CC)CC)C>[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[NH:30][C:11](=[O:12])[C:10]1[CH:14]=[C:15]([O:21][CH3:22])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:8]([F:7])[CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 234322-MethylcyclohexylamineHCID 574456983-Fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701201N-(2-methylcyclohexyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5 ml of ethyl acetate and 0.30 g of 3-fluoro-5-methoxy-4-(2-propynyloxy)benzoyl chloride were added 0.15 g of 2-methylcyclohexylamine and 0.40 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 2 hours. Then, the reaction product was subjected to silica gel column chromatography to obtain 0.34 g of N-(2-methylcyclohexyl)-3-fluoro-5-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 48 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained

Sources & evidence

ORD record
ord-283a9596c84b4f5995bd061e616d8e96
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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