Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86630186, compound

Participants

Reaction Steps

5-nitro-1-trityl-1H-indazole-3-carboxylic acid 20AP (12.06 g, 26.85 mmol) and HATU (10.2 g, 26.85 mmol) was dissolved in DMF (100 ml). After stirring for 10 min at room temperature, N,O-dimethylhydroxylamine hydrochloride 21AP (2.62 g, 26.85 mmol) and DIEA (14.1 ml, 80.55 mmol) was added. It was stirred further for 1 hr at room temperature. Reaction mixture was poured into 300 ml of water. Solid was collected by filtration. This solid was redissolved in EtOAc (300 ml) and 75 ml of sat. NaHCO3 was added. Organic fraction was washed with water (2×75 ml), brine (75 ml) and dried over MgSO4. Solvent was removed under reduced pressure to give desired 5-nitro-1-trityl-1H-indazole-3-carboxylic acid methoxy-methyl-amide 22AP (12.56 g, 95%).

Provenance & Evidence