反応 #72307
ord-d9314c00c9fe40b7820024c97a939dde
反応方程式
反応物
試薬
溶媒
反応条件
後処理
- 1濃縮concentrated
- 2その他The resultant residue was purified
実験手順
To a solution containing 2-phenylpropan-2-amine (0.030 g, 0.23 mmol), diisopropylethylamine (0.13 mL, 0.75 mmol), 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzo[b]thiophen-5-yl)benzoic acid (0.075 g, 0.15 mmol) and DMF (1.0 mL) was added HATU (0.74 g, 0.20 mmol) in one portion. The solution was maintained at room temperature for 15 h and concentrated. The resultant residue was purified using preparative HPLC (Waters—Xbridge, 50×100 mm, 5 micron, C18 column; 0.1M ammonium acetate, 0-100% B (B=5% H2O/CH3CN)/A (A=95% H2O/CH3CN), 10 min. gradient) afforded 2-(4-fluorophenyl)-N-methyl-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzo[b]thiophene-3-carboxamide as a white solid. Preparative HPLC: retention time: 8.5 min. 1H NMR (500 MHz, DMSO-D6) δ ppm 8.62 (s, 1H), 8.42 (d, J=4.88 Hz, 1H), 8.17 (d, J=8.55 Hz, 1H), 8.13 (s, 1H), 7.99 (s, 1H), 7.84-7.89 (m, 2H), 7.82 (dd, J=8.55, 1.53 Hz, 1H), 7.66 (dd, J=8.70, 5.34 Hz, 2H), 7.59 (t, J=7.78 Hz, 1H), 7.42 (d, J=7.32 Hz, 2H), 7.37 (t, J=8.70 Hz, 2H), 7.30 (t, J=7.63 Hz, 2H), 7.18 (t, J=7.32 Hz, 1H), 2.77 (d, J=4.58 Hz, 3H), 1.71 (s, 6H). LCMS: retention time: 3.305 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 10 micron, C18, 4.6×50 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 4 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3OH/90% H2O/10 mM TFA and solvent B was 10% H2O/90% CH3OH/10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 523 (MH+).