Triethylamine → HCID 11989753, 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-(Hydroxymethyl)piperidine (Maybridge)(76.3 mg; 0.66 mmol; 1 eq.) and triethylamine (0.19 ml; 1.33 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 (27) as a brown solid (106.3 mg; 42%). 1H NMR (DMSO-d6, 300 MHz) δ 1.05-1.30 (m, 2H), 1.65-1.87 (m, 3H), 2.14 (s, 3H), 2.50 (s, 3H), 2.86 (m, 1H), 3.20 (m, 1H), 3.28 (m, 2H), 4.48 (m, 1H), 4.52 (t, J=4.5 Hz, 1H), 5.16 (m, 1H), 7.97 (s, 1H), 12.16 (s, 1H). M− (ESI): 379.20; M+ (ESI): 381.19. HPLC (method A), Rt: 2.47 min (purity: 99%).

Provenance & Evidence