[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15]C(=O)C)[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:21][CH:22]([CH3:24])[CH3:23].[OH-].[Na+].O.Cl>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:21][CH:22]([CH3:24])[CH3:23]
N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (123.6 mg, 342.5 μmol) was suspended in MeOH (2.2 ml) and sodium hydroxide (89.90 mg, 2248 μmol) and water (0.44 ml) were added. The reaction flask was fit with a reflux condenser and placed in a preheated oil bath (80° C.), and the reaction was stirred for 1 hour. The reaction was cooled to room temperature, treated with 5 N HCl to neutralize the solution, and allowed to stand overnight. It was then extracted with 10:1 DCM/MeOH, and the organic extracts were combined, concentrated, and purified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH). Fractions with product collected, concentrated, and treated with Et2O and MeOH. The MeOH washings were decanted, and the solid was collected and dried under high vacuum to afford 6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (18.2 mg, 17% yield). MS (ESI pos. ion) m/z: 319. Calculated exact mass for C15H15ClN4S 318.
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