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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Reaction Steps

To a solution of (S)-methyl-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (400 mg, 1.22 mmol) in MeOH (15 mL) was added a 1M aqueous solution of LiOH (3.66 mL, 3.66 mmol). After 30 min, the organic solvent was removed under reduced pressure, and the pH of the aqueous layer was adjusted to pH=3 with 2N HCl, extracted with CH2Cl2 (3×50 mL). The combined organic layers were concentrated to give the (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid (325 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, J=6.6 Hz, 3H), LRMS [M+H]+: 311 m/z.

Provenance & Evidence