[C:1]([C:3]1[C:4]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])=[N:5][C:6]([NH:9][C:10]2[N:11]=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][N:8]=1)#[N:2].[OH-].[Li+].CO>C1COCC1>[C:1]([C:3]1[C:4]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[N:5][C:6]([NH:9][C:10]2[N:11]=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][N:8]=1)#[N:2]Ethyl 2-(3-cyano-6-(isoquinolin-3-ylamino)pyrazin-2-yloxy)acetate (35 mg, 0.099 mmol) was dissolved in THF (1 mL) and lithium hydroxide (2.4 mg, 0.099 mmol) added. The reaction was stirred at room temperature for 15 hours. Methanol (1 mL) was added and the reaction mixture was stirred for a further 24 hours and then concentrated to dryness. Purification by preparative HPLC afforded the title compound (10.8 mg, 0.0336 mmol, 34%). 1H NMR (MeOD, 400 MHz) δ 9.04 (s, 1H), 8.53 (s, 1H), 8.14-8.10 (m, 2H), 7.97 (d, 1H, J=8.0 Hz), 7.72-7.67 (m, 1H), 7.53-7.48 (m, 1H), 4.96 (br s, 2H), 2.67 (s, 1H). LC-MS (2) Rt=1.46 min; No ionization.
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