Cesium fluoride → (S)-4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-N-(4-(N-methylsulfamoyl)phenyl)pyrimidine-5-carboxamide

Temperature

80 °C

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (100 mg, 0.33 mmol), 4-amino-6-chloro-N-(4-(N-methylsulfamoyl)phenyl)pyrimidine-5-carboxamide (123 mg, 0.36 mmol), DIEA (344 μl, 1.97 mmol) and cesium fluoride (150 mg, 0.99 mmol) were suspended in tert-butanol (10 ml) and the mixture was heated at 80° C. in a sealed tube for 24 h. The solvent was evaporated under reduced pressure and the reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution and brine. After evaporation of the solvent, the residue was purified by reverse phase chromatography using SP1® Purification System to give 47 mg (23% yield) as a solid. Purity 94%.

1. customThe solvent was evaporated under reduced pressure
2. additionthe reaction mixture was diluted with ethyl acetate
3. washwashed with saturated ammonium chloride solution and brine
4. customAfter evaporation of the solvent
5. customthe residue was purified by reverse phase chromatography
6. customSP1® Purification System
7. customto give 47 mg (23% yield) as a solid

ORD record

ord-0730ddda68f4452ab2b5175793ec6bdc

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388189B2