Dimethyl Sulfoxide → 6-{[2-({2-(Morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidin-5-yl}amino)ethyl]amino}pyridine-3-carbonitrile

HRID 2389852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389852
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:10]=[C:6]2[CH:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:3]=1.FC(F)(F)C(O)=O.[NH2:35][CH2:36][CH2:37][NH:38][C:39]1[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][N:40]=1.CS(C)=O.CCN(C(C)C)C(C)C>C(OCC)(=O)C>[N:12]1([CH2:11][C:9]2[N:10]=[C:6]3[N:7]([C:2]([NH:35][CH2:36][CH2:37][NH:38][C:39]4[N:40]=[CH:41][C:42]([C:43]#[N:44])=[CH:45][CH:46]=4)=[N:3][C:4]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)=[CH:5]3)[N:8]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 593131385-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidineHCID 687096656-[(2-Aminoethyl)amino]nicotinonitrile trifluoroacetate

Produkt 1

HCID 687136806-{[2-({2-(Morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidin-5-yl}amino)ethyl]amino}pyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

300 mg (0.75 mmol) of 5-chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)-phenyl][1,2,4]triazolo[1,5-c]pyrimidine (Example 151A) and 180 mg (0.91 mmol) of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (Example 13A) are introduced into DMSO (4 ml), 0.79 ml (4.5 mmol) of DIEA is added, and the reaction solution is irradiated in a microwave reactor at 140° C. for 30 min. The reaction mixture is diluted with ethyl acetate, and the organic phase is washed with saturated sodium bicarbonate solution, ammonium chloride solution and saturated sodium chloride solution, dried and concentrated. The residue is taken up in acetonitrile (4 ml), and the solid which precipitates is filtered off and dried. 300 mg (76% of theory) of the product are obtained as a solid.

Aufarbeitung

  1. additionis added
  2. customthe reaction solution is irradiated in a microwave reactor at 140° C. for 30 min
  3. washthe organic phase is washed with saturated sodium bicarbonate solution, ammonium chloride solution and saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customthe solid which precipitates
  7. filtrationis filtered off
  8. customdried
  9. custom300 mg (76% of theory) of the product are obtained as a solid

Quellen und Nachweise

ORD-Eintrag
ord-8931f93288b74c31a87f4c532b1f34e6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273752B2

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