Triethylamine → HCID 11989861, compound

Participants

Reaction Steps

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above, (166.6 mg, 0.55 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-Hydroxypiperidine (Fluka)(55.8 mg; 0.55 mmol; 1 eq.) and triethylamine (0.15 ml; 1.10 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (29) as a brown solid (80.3 mg; 40%). 1H NMR (DMSO-d6, 300 MHz) δ 1.44 (m, 2H), 1.82 (m, 2H), 2.14 (s, 3H), 2.50 (s, 3H), 3.35 (m, 2H), 3.80 (m, 2H), 4 (m, 1H), 4.60 (m, 1H), 7.98 (s, 1H), 12.16 (br s, 1H). M− (ESI): 365; M+ (ESI): 367. HPLC (method A), Rt: 2.31 min (purity: 91.1%).

Provenance & Evidence