Triethylamine → HCID 11990110, compound

Participants

Reaction Steps

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-Fluoropyperidine (Flrochem) (95.7 mg; 0.92 mmol; 1.40 eq.) and triethylamine (0.37 ml; 2.65 mmol; 4 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is purified by preparative HPLC, affording Compound (48) as a white-off powder (36 mg; 13%). 1H NMR (DMSO-d6, 300 MHz) δ 1.71-2.12 (m, 4H), 2.16 (s, 3H), 2.50 (s, 3H), 3.75 (m, 2H), 4.33 (m, 2H), 4.97 (ttd, J=3, 6, 51 Hz, 1H, —CFH), 8.02 (s, 1H), 12.19 (s, 1H). M− (ESI): 367.13; M+ (ESI): 369.12. HPLC (method A), Rt: 3.04 min (purity: 95.8%).

Provenance & Evidence