[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1.[C:18](Cl)(=[O:20])[CH3:19].C(O)C(N)(CO)CO>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1To a vial charged with 3-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine (100 mg, 0.306 mmol), PS-DMAP (Argonaut resin, 1.2 g, 6 equiv.), and a stirring bar was added THF (3 mL) and acetyl chloride (110 μL, 1.53 mmol). The reaction mixture was stirred at 70° C. for 1 hour, then cooled to room temperature and treated with PS-trisamine (Argonaut resin, 1.1 g, 20 equiv.) for 1 hour. The resin was filtered, washed with THF and the solvent was evaporated. The resulting crude was suspended in MeOH and treated with hydrazine monohydrate (0.06 mL) for 30 minutes. The precipitate was filtered, and the filtrate was directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide 12.5 mg (14% yield) of N-[3-(4-methoxy-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-yl]-acetamide as an off-white solid. 1H-NMR (d6-DMSO) δ: 13.4 (broad s, 1H), 12.3 (broad s, 1H), 7.66 (broad s, 2H), 7.09 (broad s, 2H), 3.80 (s, 3H), 2.18 (s, 3H); HPLC/MS m/z: 289.0 [MH]+.
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