HCID 118383913, compound → HCID 118383914, compound

Participants

Reaction Steps

Pd/C (9.0 mg, 8.5 μmol) was added to a stirring solution of (E)-5-(3-((2-(1,2,4-oxadiazol-3-yl)propan-2-yl)carbamoyl)phenyl)-2-(4-fluorophenyl)-N-methyl-6-(prop-1-en-1-yl)furo[2,3-b]pyridine-3-carboxamide (23 mg, 0.043 mmol) in MeOH (853 μl) at room temperature. The reaction mixture was placed in a Parr bomb and charged with 25 PSI of H2 (g) and the reaction mixture was allowed to stir for 4 hours. LCMS indicated no conversion. Pd/C (9.0 mg, 8.5 μmol) was added and the reaction mixture was placed in a Parr bomb and charged with 50 PSI of H2 (g) and the reaction mixture was allowed to stir for 16 hours. The reaction mixture was filtered and purified by preparative reverse phase HPLC on a C18 column using a suitably buffered H2O/CH3CN gradient, and concentrated to give 5-(3-((2-cyanopropan-2-yl)carbamoyl)phenyl)-2-(4-fluorophenyl)-N-methyl-6-propylfuro[2,3-b]pyridine-3-carboxamide (2.5 mg, 4.7 μmol, 11% yield) consistent by LCMS and NMR. 1H NMR (400 MHz, CDCl3) δ 8.01-7.95 (m, 2H), 7.94 (s, 1H), 7.82 (d, J=7.5 Hz, 1H), 7.70 (s, 1H), 7.56-7.45 (m, 2H), 7.22 (t, J=8.7 Hz, 2H), 6.58 (s, 1H), 6.09-6.01 (m, 1H), 2.99 (d, J=5.0 Hz, 3H), 2.74-2.67 (m, 2H), 1.86 (s, 6H), 1.71-1.65 (m, 2H), 0.85 (t, J=7.4 Hz, 3H). LC-MS retention time: 2.05 min; m/z (M+H)+: 499. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 10% methanol/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% methanol/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

Provenance & Evidence