反応 #2017171

反応方程式

2-bromo-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2,4,5-trifluorophenyl)ethanone

tert-butyl 4-(aminocarbothioyl)tetrahydropyridine-1-(2H)-carboxylate

→

title compound

収率 34.0%

tert-Butyl 4-(5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4-(2,4,5-trifluorophenyl)thiazol-2-yl)piperidine-1-carboxylate

収率 34.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他The reaction was quenched with saturated aqueous NaHCO3
2. 2
   抽出extracted with Et2O (300 mL)
3. 3
   乾燥The organic layer was dried over Na2SO4
4. 4
   その他decanted
5. 5
   濃縮concentrated
6. 6
   洗浄eluted with a gradient of 0-10% MeOH in DCM

実験手順

A mixture of 2-bromo-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2,4,5-trifluorophenyl)ethanone (0.90 g, 2.2 mmol; prepared using General Procedure J from Preparation #F.1 and Preparation #G.1, General Procedure K with H2SO4, and General Procedure A.2), tert-butyl 4-(aminocarbothioyl)tetrahydropyridine-1-(2H)-carboxylate (Maybridge, 0.8 g, 3.3 mmol) and DMF (20 mL) was stirred at ambient temperature for about 24 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with Et2O (300 mL). The organic layer was dried over Na2SO4, decanted, and concentrated. The crude material was loaded onto a silica gel column and eluted with a gradient of 0-10% MeOH in DCM to give the title compound (0.41 g, 34%): LC/MS (Table 1, Method a) Rt=4.18 min; MS m/z: 559.3 (M+H)+.

出典