Citric Acid → 6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

참여 물질

역할	이름	HCID	투입량
반응물	Citric Acid	HCID 311	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	HOAt	HCID 181649	—
반응물	4-Methylsulfonylbenzylamine hydrochloride	HCID 2729269	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	6-Methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid	HCID 11702104	—
용매	Water	HCID 962	—
용매	N-methyl-2-pyrrolidone	HCID 13387	—
생성물	6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide	HCID 11619625	70%

반응 단계

A mixture of 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (7.43 g, 25 mmol), HATU (10.5 g, 27.5 mmol), HOAT (3.75 g, 27.5 mmol) and DIEA (14.2 ml, 82.5 mmol) in NMP (65 ml) was reacted for 1 h, then 4-methylsulphonylbenzyl amine hydrochloride (5.8 g, 26 mmol) was added. After 1 h, the reaction mixture was slowly poured into stirred ice water (1 L). A powder was formed and the water mixture was acidified to pH 3 with 0.5M citric acid, and stirring was continued for 1 h. The precipitate was filtered off, washed with water and dried in vacuum overnight. Recrystallisation from EtOAc gave 6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (8.1 g, 70%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07998984B2
출처 데이터셋	uspto-grants-2011_08
ORD ID	ord-89f5187f0add4a87805ee95f944490d5
출처 메모	uspto-grants-2011_08