Hydrochloric Acid → HCID 56595705, compound

Participants

Reaction Conditions

Reaction Steps

To a soln. of (S)-2-(2-chloro-5H-chromeno[2,3-b]pyridin-5-yl)-2-methylpropanoic acid (30b, 10 g, 32.9 mmol) in acetonitrile (200 ml) was added triethylamine (22.94 ml, 165 mmol), O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N′,N′-TETRAMETHYLURONIUM PF6 (HATU) (16.27 g, 42.8 mmol) and 1,3,4-thiadiazol-2-amine (9.99 g, 99 mmol). The resulted mixture was heated at 80° C. for 12 h. The reaction mixture was then concentrated in vacuum and the residue was partitioned between EtOAc and 1N HCl. The obtained organic layer was washed with saturated NaHCO3, brine, then dried (Na2SO4) and concentrated to give a solid. The solid was dissolved in EtOH (400 mL) with gentle warming. Added 1N HCl (˜200 mL) portionwise. The solid was collected and washed with water, dried on vacuum pump overnight to give 10 g (79%) of (S)-2-(2-chloro-5H-chromeno[2,3-b]pyridin-5-yl)-2-methyl-N-(1,3,4-thiadiazol-2-yl)propanamide (53a). MS (E+) m/z: 387 (M+H); LC retention time: 3.12 min.

Provenance & Evidence