Pyridine → HCID 178474446, compound

Participants

Reaction Conditions

Reaction Steps

2-Ethylhexyl chloroformate (101.22 μl; 0.51 mmol; 1.00 eq.) is added dropwise to an ice cooling mixture of 3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}-N-hydroxybenzenecarboximidic acid (60) obtained as described above in Example 60 (200.00 mg; 0.51 mmol; 1.00 eq.) and anhydrous pyridine (41.56 μl; 0.51 mmol; 1.00 eq.) in DMF (2.00 ml). The resulting mixture is stirred at 0° C. for 30 min. It is diluted with water and extracted with EtOAc (3 times). The extracts are washed with water and dried over Na2SO4. Solvents are evaporated and the resulting crude intermediate is suspended in xylene (2 mL) and heated at 150° C. for 2 hours. The solvents are evaporated and the resulting crude product is purified by flash chromatography, affording N-(2-{[3-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide (61) as parent (134.90 mg; 64.70%). A sample (88.00 mg; 0.21 mmol; 1.00 eq.) is suspended in water (2.50 ml) and THF (2.50 ml) and potassium hydroxide solution (416.15 μl; 0.50 M; 0.21 mmol; 0.98 eq.) is added. The resulting solution is filtered through cotton and freeze-dried, affording (61) as brown powder (82.8 mg; 91.58%). 1H NMR (DMSO-d6, 300 MHz) δ 2.12 (s, 3H), 2.52 (s, 3H, COCH3), 6.88 (s, 1H), 7.34 (m, 2H), 7.84 (m, 2H), 10.34 (s, 1H). M− (ESI): 413; M+ (ESI): 415. HPLC, Rt: 3.09 min (purity: 97.6%).

Provenance & Evidence