1,2-Dichloroethane → Hydrochloric Acid

Participants

Reaction Steps

Compound 163 (70 mg, 0.12 mmol) was dissolved in 8 mL 1,2-dichloroethane and 8 mL dioxane with DIEA (105 μL, 0.60 mmol). To it was added acetone (180 μL, 2.4 mmol). The mixture was stirred at RT for 2 h. To it were added acetic acid (68 μL, 1.2 mmol) and then NaBH(OAc)3 (127 mg, 0.60 mmol). The mixture was stirred for overnight. It was diluted with 2 mL water, concentrated in vacuo, treated with TFA (0.2 mL) and subjected to reverse phase preparative HPLC to isolate (R)-3-(4-(1-isopropylpiperidin-4-yl)phenylamino)-5-(3-(4-methoxybenzamido)piperidin-1-yl)pyrazine-2-carboxamide (164) as HCl salt (34 mg). MS found for C32H41N7O3 as (M+H)+ 572.3, (M−H)− 570.4. UV: λ=258, 279, 305, 335, 372 nm.

Provenance & Evidence