Methanol → HCID 87267754, compound

Participants

Reaction Conditions

Reaction Steps

To a suspended solution of 2-N—BOC-amino-4-benzothiazole-6-carboxylic acid (2.05 g, 6.97 mmol) and 2,3,4,5,6-pentafluorophenol (1.92 g, 10.4 mmol) in EtOAc (60 mL) was added 1,3-dicyclohexylcarbodiimide (2.16 g, 10.4 mmol). The mixture was heated to 45° C. for 16 hours. Small amount of MeOH was added to the mixture and the solid was removed by filtration. The filtrate was concentrated in vacuo to give pentafluorophenyl 2-(tert-butoxycarbonyl)benzo[d]thiazole-6-carboxylate as a pink material (3.50 g), which was used in the next step without further purification. A solution of pentafluorophenyl 2-(tert-butoxycarbonyl)benzo[d]thiazole-6-carboxylate (1.0 g, 2.2 mmol) and anhydrous hydrazine (0.35 ml, 11 mmol) in THF (30 mL) was stirred at room temperature for 6 hours. The mixture was then concentrated in vacuo and the residue was washed with CHCl3 containing small amount of MeOH. The solid was collected by filtration to give the product as a light yellow solid (0.30 g, 45% yield). MS (ESI pos. ion) m/z: calc'd for: C13H16N4O3S: 308.0. found: 309.0.

Provenance & Evidence