Hydrochloric Acid → HCID 178432001, compound

Participants

Reaction Conditions

Reaction Steps

A micro-tube was charged with tris(benzylideneacetone)dipalladium (Pd2(dba)3) (0.5 mg, 0.0005 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.5 mg, 0.0012 mmol) and pyrrolidine (9 mg, 0.12 mmol). The tube was sealed and flushed with nitrogen. LiHMDS (1M in THF, 120 μL, 0.12 mmol) and a solution of 5-bromo-3-methyl-N-[3-(1H-tetrazol-5-yl)phenyl]-1-benzothiophene-2-sulfonamide (Example 34) (45 mg, 0.1 mmol) in dry THF were added to the reaction mixture via syringes. The reaction mixture was heated in a microwave reactor at 130° C. for 1000 s. Aqueous HCl (1 M) was added and the mixture was stirred at room temperature for 5 min. The solution was then neutralized by addition of aqueous NaOH. The crude product was purified by preparative HPLC (ACE C8, 5 μm 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/CH3CN) to give 1.9 mg (4%) of the title compound. MS (ESI+) calcd for C20H20N6O2S2 440.108915, found 440.108815.

Provenance & Evidence