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Preparation of N1-((1S,2R,4S)-2-amino-4-(dimethylcarbamoyl)cyclohexyl)-N2-(5-chloropyridin-2-yl)oxalamide dihydrochloride

IP.com Disclosure Number: IPCOM000248438D
Publication Date: 2016-Nov-29
Document File: 1 page(s) / 11K

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Preparation of N1-((1S,2R,4S)-2-amino-4-(dimethylcarbamoyl)cyclohexyl)-N2-(5-chloropyridin-2-

yl)oxalamide dihydrochloride

Example 1Tert-butyl(1R,2S,5S)-2-(2-(5-chloropyridin-2-ylamino)-2-oxoacetamido)-5-(dimethylcarbamoyl) cyclohexylcarbamate (10.0g) was suspended in dichloromethane (50ml) at room temperature. IPA HCl
(4.9N, 28.3ml) was added and the mixture was stirred at room temperature for 18 hours. Heptane (100ml) was added and the suspension was cooled to 0-5ºC. After 1h the crude was filtered, washed and dried at 50ºC for 4h to obtain quantitatively the title compound.

Example 2Tert-butyl(1R,2S,5S)-2-(2-(5-chloropyridin-2-ylamino)-2-oxoacetamido)-5-(dimethylcarbamoyl) cyclohexylcarbamate (4.0g) was dissolved in acetonitrile (41ml) at room temperature. IPA HCl (5.5N, 10.3ml) was added and the mixture was stirred at room temperature for 2 hours. The suspension was cooled to 0- 5ºC and filtered. After 2h, the mixture was filtered, washed and dried at 50ºC for 7 hours to obtain the title compound (3.7g, 97.3% yield).

Example 3Tert-butyl(1R,2S,5S)-2-(2-(5-chloropyridin-2-ylamino)-2-oxoacetamido)-5-(dimethylcarbamoyl) cyclohexylcarbamate (8.0g) was dissolved in acetonitrile (80ml) at room temperature. Hydrochloric acid 35%
(6.7ml) was added and the mixture was stirred at room temperature for 6 hours. The suspension was cooled to 0-5ºC and filtered to obtain the title compound (7.3g, 97.1% yield).