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

HRID 1672604

Reaktionsgleichung

Reaktionsgleichung von HRID 1672604
[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

Komponenten

9

Edukt 6

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117021046-Methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 116196256-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. customwas reacted for 1 h
  2. additionthe reaction mixture was slowly poured
  3. customA powder was formed
  4. waitwas continued for 1 h
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried in vacuum overnight
  8. customRecrystallisation from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-89f5187f0add4a87805ee95f944490d5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998984B2

Verknüpfte Notizen

Wird geladen…