2-Pyridinemethanamine → HCID 90386205, compound

Participants

Reaction Conditions

Reaction Steps

N-(tert-Butyl)-4-(4-hydroxy-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)thiazole-2-sulfonamide (0.0600 g, 0.140 mmol) was dissolved in acetonitrile (5 mL) and cooled to 0° C. BOP reagent (0.0620 g, 0.140 mmol) was added slowly, followed by DBU (0.0210 mL, 0.140 mmol). The reaction mixture was allowed to reach ambient temperature for 1 h then cooled to 0° C. Pyridin-2-ylmethanamine was added, (0.0150 g, 0.140 mmol). The reaction mixture was allowed to reach ambient temperature and stir for 14 h and diluted with water. The aqueous mixture was extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 1.2% methanol in CH2Cl2) to afford N-(tert-butyl)-4-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)thiazole-2-sulfonamide (0.0400 g, 55.0%). The impure compound was taken to the next step as such. LCMS Condition B-13: retention time 2.13 min, [M+1]=520.2.

Provenance & Evidence