2-Mercaptoethanol → HCID 23654508, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of crude N—((S)-3-(3-chlorophenyl)-2-(4-nitrophenylsulfonamido)propyl)-N-(5-(isoquinolin-6-yl)thiazol-2-yl)acetamide (0.33 g, 0.535 mmol) in EtOH (3 mL), was added sodium hydroxide (1.1 mL, 1 M aqueous solution, 1.1 mmol) at room temperature. After addition, the reaction mixture was stirred at 80° C. overnight. The reaction mixture was then diluted with NH4Cl (10 mL (aqueous)) and water (10 mL), and diluted with DCM (5 mL). The separated aqueous layer was extracted with EtOAc (5 mL×2), and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude residue (0.2233 g, 385 μmol), to which DMF (2 mL), 2-mercaptoethanol (60 mg, 770 μmol), and K2CO3 (160 mg, 1155 μmol) were added sequentially. The resulting mixture was stirred at room temperature for 1.5 hours, and the resulting dark mixture was diluted with NH4Cl (5 mL (aqueous)) and water (5 mL) and diluted with DCM (5 mL). The separated aqueous layer was extracted with DCM (10 mL×2), and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude residue which was purified with flash column chromatography (pure DCM→5% MeOH in DCM) to obtain the desired product N—((S)-2-amino-3-(3-chlorophenyl)propyl)-5-(isoquinolin-6-yl)thiazol-2-amine (33 mg, 84 μmol) as a yellow solid.

Provenance & Evidence