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

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Reaction Steps

Sodium cyanoborohydride (37 mg, 0.59 mmol) and methylamine (170 μL, 0.34 mmol) were added to a solution of 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one (50 mg, 0.107 mmol, from example 75) in MeOH (1.1 mL). The mixture was stirred at rt for 4 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/mM, 30-95% B, 20 min to afford 5.0 mg (9% yield) of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(4-fluorophenyl)-N6-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine. LC-MS (M+H)+ 484.2.

Provenance & Evidence