Dimethylamine → 2-(2-(4-((Dimethylamino)methyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

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Reaction Steps

2-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (30 mg, 0.068 mmol), Dimethylamine (2M solution in THF, 0.169 mL, 0.34 mmol) and DMF (1 mL) were treated with acetic acid (5 drops) and sodium triacetoxyborohydride (57.2 mg, 0.270 mmol) and the mixture stirred at RT overnight. The sample was filtered and purified by preparative reverse phase HPLC followed by additional purification by SCX ion exchange chromatography to yield the title compound (13.5 mg, 0.029 mmol, 42%).

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