Example 11 : Λ/-(1-(1-(2-hvdroxyethvh-5-methyl-1H-pyrazol-4-vhethvh-2- (2,2.2-trifluoro-1.1 -dimethylethvOαuinoline-β-carboxamtde
To a solution of Example 10 (23 mg, 0.05 mmol) in THF (3 ml) was added LiBH4 powder (3.25 mg, 0.15 mmol) at rt, and the resulting mixture was heated at 65 0C, then MeOH (3 drops) was added and the resulting mixture was heated at the same temperature for 60 min. After being cooled to rt, the reaction mixture was quenched by addition of sat. NH4CI aq. and the aqueous layer was extracted with AcOEt 3 times. The combined organic extracts were washed with water and brine successively, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by HPLC (column: MS C 30 x 50 mm, acetonitrile: 0.01 % NH3 aq =96:4 to 4:96 as eluent) to give the title compound as a white solid (16.6 mg, 77% yield). 1H NMR (300 MHz, DMSO-Of6) δ 1.50 (3H, d, J = 6.0 Hz), 1.71 (6H1 s), 2.26 (3H, s), 3.67 (2H, dd, J = 6.0, 12.0 Hz)1 4.03 (2H1 t, J = 6.0 Hz), 4.84 (1 H, t, J = 6.0 Hz)1 5.14-5.24 (1 H, m), 7.46 (1 H1 s), 7.87 (1 H1 d, J = 9.0 Hz)1 8.07 (1H1 d, J = 9.0 Hz), 8.19-8.23 (1 H1 m), 8.50-8.53 (2H1 m), 8.85 (1 H1 brd, J = 6.0 Hz). MS (ESI) m/z 433 (M - H)" , 435 (M + H)+.
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