Diisopropylethylamine → N-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamide

HRID 511205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511205
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][CH2:14][C:15]1[C:16]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:17][CH:18]=[CH:19][CH:20]=1.C(N(C(C)C)CC)(C)C>>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH2:14][C:15]2[C:16]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:17][CH:18]=[CH:19][CH:20]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:13][CH2:14][C:15]2[C:16]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:17][CH:18]=[CH:19][CH:20]=2)[N:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

Produkt 2

HCID 57584561N-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)-N-methylmethanesulfonamideHCID 86653992N-[3-({[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}methyl)pyridin-2-yl]-N-methylmethanesulfonamide

Versuchsvorschrift

Reaction of 2,4-dichloro-5-(trifluoromethyl)pyrimidine XL with N-[3-(aminomethyl)pyridin-2-yl]-N-methylmethanesulfonamide (WO2007/072158, WO2008/115369) in the presence of diisopropylethylamine affords a solution of N-[3-({[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}methyl)pyridin-2-yl]-N-methylmethanesulfonamide XLIa and its regioisomer N-[3-({[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}methyl)pyridin-2-yl]-N-methylmethanesulfonamide XLIb. On larger scales stirring at 0° C., precipitation of the pure 4-substituted isomer XLIa occurs. Reaction of a sample of the pure mixture of N-[3-({[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}methyl)pyridin-2-yl]-N-methylmethanesulfonamide with anilines such as 4-[(diethylphosphoryl)methyl]aniline in the presence of TFA and TFE under microwave irradiation yields 2-substituted N-methyl-N-[3-({[5-(trifluoromethyl)pyrimidin-4-yl]amino}methyl)pyridin-2-yl]methanesulfonamides (e.g. N-[3-({[2-({4-[(diethylphosphoryl)methyl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}methyl)pyridin-2-yl]-N-methylmethanesulfonamide, Example 10).

Quellen und Nachweise

ORD-Eintrag
ord-a71b265d325748d6bca5ae649a39389b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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