C([O:4][CH:5]([CH3:23])[C:6]([N:8]([C:11]1[C:12]([Cl:22])=[N:13][N:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:15]=1)[CH2:9][CH3:10])=[O:7])(=O)C.[OH-].[Li+].Cl>CO.C1COCC1>[Cl:22][C:12]1[C:11]([N:8]([CH2:9][CH3:10])[C:6](=[O:7])[CH:5]([OH:4])[CH3:23])=[CH:15][N:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[N:13]=1
To a stirred solution of 1-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)amino)-1-oxopropan-2-yl acetate (2.4 g, 7.1 mmol) in MeOH (9 mL) and THF (9 mL) was added lithium hydroxide (LiOH, 2 M, 7.0 mL, 14 mmol). The reaction mixture was stirred for two hours at room temperature, and then the reaction mixture pH was made neutral by the addition of aq. 2M HCl. After the mixture was then extracted with EtOAc, the organics phases were combined, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound C13 as a white solid (1.9 g, 88%): mp 137-138° C.; 1H NMR (400 MHz, DMSO) δ 9.08 (d, J=2.5 Hz, 1H), 8.98 (s, 1H), 8.58 (dd, J=4.7, 1.1 Hz, 1H), 8.23 (ddd, J=8.4, 2.6, 1.3 Hz, 1H), 7.59 (dd, J=8.3, 4.7 Hz, 1H), 4.97 (d, J=7.6 Hz, 1H), 4.08 (m, 1H), 3.57 (d, J=50.6 Hz, 2H), 1.10 (d, J=6.5 Hz, 3H), 1.07 (t, J=7.1 Hz, 3H); ESIMS m/z 295.6 ([M+H]+).
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