2-methylcyclopentan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.12 g of 2-methylcyclopentylamine, 0.2 ml of triethylamine and 1 ml of ethyl acetate was added dropwise under ice cooling to a mixture of 1 ml of ethyl acetate and 0.23 g of 3,5-difluoro-4-(2-propynyloxy)benzoyl chloride. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was subjected to silica gel column chromatography to obtain 0.07 g of N-(2-methylcyclopentyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 54 of the present invention) represented by the formula: The mixture obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.12 g of 2-methylcyclopentylamine, 0.2 ml of triethylamine and 1 ml of ethyl acetate was added dropwise under ice cooling to a mixture of 1 ml of ethyl acetate and 0.23 g of 3,5-difluoro-4-(2-propynyloxy)benzoyl chloride. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was subjected to silica gel column chromatography to obtain 0.07 g of N-(2-methylcyclopentyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 54 of the present invention) represented by the formula: The mixture obtained

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 9.32 g of 4-fluoro-3-nitro-benzoic acid methyl ester in 30 ml of abs. DMF was added 16.47 g of potassium carbonate, followed by 5.00 g of 2-methyl-cyclopentylamine. After 16 h at rt, the mixture was poured into water, the pH was adjusted to 5 by the addition of 2 M aqueous hydrochloric acid, and the reaction mixture was extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over sodium sulphate and concentrated to yield 12.74 g (100%) of 4-(2-Methyl-cyclopentylamino)-3-nitro-benzoic acid methyl ester. the reaction mixture was extracted with ethyl acetate three times The combined organic phases were washed with water dried over sodium sulphate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.12 g of 2-methylcyclopentylamine, 0.2 ml of triethylamine and 1 ml of ethyl acetate was added dropwise under ice cooling to a mixture of 1 ml of ethyl acetate and 0.23 g of 3,5-difluoro-4-(2-propynyloxy)benzoyl chloride. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was subjected to silica gel column chromatography to obtain 0.07 g of N-(2-methylcyclopentyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 54 of the present invention) represented by the formula: The mixture obtained