ORGANIC SPECTROSCOPY INTERNATIONAL: WO2008059370A2

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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