Formaldehyde → N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6,N6-dimethyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

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Reaction Steps

Sodium cyanoborohydride (14.53 mg, 0.231 mmol) and formaldehyde (16.15 μL, 0.217 mmol) were added to a solution of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (18 mg, 0.038 mmol, from example 78) in MeOH (0.4 mL). The mixture was stirred at rt for 20 hours. The crude reaction mixture was purified using preparatory HPLC (Column: Phenomenex Luna C18 30×100 mm, Solvent A=10 mM Ammonium Acetate in 95:5 water/ACN, Solvent B=10 mM Ammonium Acetate in 5:95 water/ACN. Flow rate: 40 ml/min, 30-95% B, 20 min to afford 10 mg (47% yield) of the titled compound as a white solid. LC-MS (M+H)+ 498.3.

Provenance & Evidence