Lithium Hydroxide → (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid

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A mixture of compound (S)-methyl 3-methyl-6-(methyl (1-phenylethyl) amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (400 mg, 1.22 mmol) and LiOH (88 mg, 3.66 mmol) in MeOH (15 mL) was stirred at room temperature for 0.5 h and then concentrated in vacuum. The residue was dissolved with DCM (100 mL), adjusted pH to 3 with 2 N aq. HCl and washed with brine (20 mL). The organic layer was evaporated in vacuum to give product (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid as a yellow solid (330 mg, 85%). 1H NMR (300 MHz, CDCl3) δ: 7.95 (s, 1H), 7.29˜7.42 (m, 5H), 5.83˜5.85 (s, 1H), 2.98 (s, 3H), 2.70 (s, 3H), 1.70 (d, 3H, J=6.6 Hz). LRMS (M+H+) m/z: calcd 312; found 312.

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