Water → HCID 178461718, compound

Participants

Reaction Steps

To a solution of (2R,4R)-(−)-pentanediol (31.2 mg) in dry DMF (1 mL) NaH (12 mg, 60% dispersion in mineral oil) was added, and the mixture was stirred at room temperature for 20 minutes under nitrogen. To this mixture 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-trifluoromethyl-phenyl)-1H-benzoimidazol-2-yl]-amide (45.6 mg) was added. The reaction was monitored by LCMS until substantially complete. Then, 10 mL of water was added and the reaction mixture was stirred for 10 minutes. The reaction was then filtered through a fine fritted funnel and the crude product was washed with water. After air drying, purified by column chromatography to obtain 6-((1R,3R)-3-hydroxy-1-methyl-butoxy)-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-trifluoromethyl-phenyl)-1H-benzoimidazol-2-yl]-amide (25.2 mg). LCMS (m/z): 526.1. 1H NMR (400 MHz, CDCl3) δ 8.39 (1H, s) 7.89 (1H, s) 7.45-7.85 (7H, m) 6.79 (1H, d) 5.42 (1H, ddd) 3.95 (1H, d) 2.18 (1H, brs) 1.91 (1H, ddd) 1.69-1.79 (1H, m) 1.44 (3H, d) 1.26 (3H, d)

Provenance & Evidence