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

HRID 559787노트

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[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5]([C:19]([OH:21])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:66][S:67]([C:70]1[CH:77]=[CH:76][C:73]([CH2:74][NH2:75])=[CH:72][CH:71]=1)(=[O:69])=[O:68].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1C(=O)CCC1.O>[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5]([C:19]([NH:75][CH2:74][C:73]2[CH:72]=[CH:71][C:70]([S:67]([CH3:66])(=[O:69])=[O:68])=[CH:77][CH:76]=2)=[O:21])=[CH:4][CH:3]=1

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실험 절차

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 citric acid (0.5 M), and stirring was continued for 1 h. The precipitate was filtered off, washed with water and dried in vacuum overnight. Recrystallisation from EtOAc gave 8.1 g (70%).

후처리

customwas reacted for 1 h
additionthe reaction mixture was slowly poured
customA powder was formed
waitwas continued for 1 h
filtrationThe precipitate was filtered off
washwashed with water
customdried in vacuum overnight
customRecrystallisation from EtOAc
customgave 8.1 g (70%)

출처 및 근거

ORD 기록: ord-6ff87138fcc94565bbfaa2e78b9dc626
출처 데이터셋: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08063073B2

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생성물 1

시약·촉매·용매 2

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