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Example 45 7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl-pyridin-2-ylmethyl-amide The title compound was provided by the reaction of 7-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid and <strong>[100155-73-5]ethyl-pyridin-2-ylmethyl-amine</strong> in a procedure analogous to Examples 1-34. MS (APCI) 555 (M+1)+; 553 (M-1)-
To a 8 mL vial charged with imidazole (17.3 mg, 0.26 mmol) and tert-butyl (6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (26.5 mg, 0.051 mmol) in DCM (1ml) was added 1,1'-carbonyldiimidazole (25 mg, 0.153 mmol). The reaction mixture was stirred at room temperature for 5 h, leading to a clear yellow solution. A solution of <strong>[100155-73-5]1-(pyridin-2-yl)propan-1-amine</strong>, 2HCl (21.33 mg, 0.102 mmol) and DIEA (0.045 ml, 0.255mmol) in DMF (1 ml) was added. The vial was capped and the contents stirred at room temperature for 16 h. The reaction mixture was concentrated and the resulting residue redissolved in TFA (1 ml) and stirred at room temperature for 20 minutes. Triethylsilane (0.008 ml, 0.051 mmol) was added dropwise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford 1-(3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(pyridin-2-yl)propyl)urea (4.1 mg, 0.012 mmol, 23.69 % yield) as a white solid.
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