Dimethylformamide → HCID 11338034, compound

Participants

Reaction Steps

The product from Example 70, Step 2 (80 mg, 0.30 mmol) was dissolved in CH2Cl2 (4 mL) under Argon. DMF (20 μL) was added, followed by oxalyl chloride (27 μL, 0.30 mmol). This mixture was stirred at rt for 30 min, then the resultant yellow solution was added to a solution of 1H-indazol-5-amine (44 mg, 0.33 mmol) in pyridine (3 mL) at −15° C. under Ar. After stirring at −15° C. for 15 min, the reaction mixture was allowed to warm to rt over 1 h. The mixture was poured into EtOAc (50 mL), washed sequentially with aq. NH4Cl (20 mL), NaOH (10 mL, 2.5 N), HCl (10 mL, 1.0 N) and then brine. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was triturated with 10% ethyl acetate/10% ether/80% hexanes to afford the title compound (56 mg, 49%). MS (ES+) m/e 383 [M+H]+.

Provenance & Evidence