Tris(hydroxymethyl)aminomethane → HCID 178496261, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-phenyl-1H-pyrazolo[3,4-d]thiazol-5-ylamine (30 mg, 0.139 mmol), PS-DMAP (Argonaut resin, 6 equiv.), and a stirring bar was added THF (2 mL) and 2-(2-methoxyethoxy)acetyl chloride (106 μL, ca. 5 equiv.). The reaction mixture was stirred at 70° C. for 24 h, then cooled to room temperature and treated with PS-trisamine (Argonaut resin, 20 equiv.) for 1.5 h. The resin was filtered, washed with THF and the solvent was evaporated. The residue was treated with a (5:1:1) mixture of THF/H2O/Et3N (2 mL) at 50° C. for 24 h, then the solution was directly adsorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2Cl2 as eluent provided 30 mg (65%) of 2-(2-methoxy-ethoxy)-N-(3-phenyl-1H-pyrazolo[3,4-d]thiazol-5-yl)-acetamide as a white solid. 1H-NMR (d6-DMSO) δ: 13.5 and 13.6 (2 broad s, 1H, NH+tautomer), 12.2 (broad s, 1H, NH), 7.74 (m, 2H, tautomers), 7.54 (m, 2H, tautomers), 7.38 (m, 1H, tautomers), 4.28 (s, 2H), 3.68 (t, 2H), 3.51 (t, 2H), 3.29 (s, 3H); HPLC/MS m/z: 333 [MH]+.

Provenance & Evidence