Réaction #434667

Équation de réaction

3-fluoro-4-(pyrrolo[2,1-f][1,2,4]-triazin-4-yloxy)benzenamine

3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

Compound C

3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

sodium thiocyanate

4-fluorophenyl-acetyl chloride

→

title compound

Rendement 83.4%

1-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)-acetyl)thiourea

Rendement 83.4%

Solvants

dichloromethane

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 4 h
2. 2
   Concentrationbefore being concentrated in vacuo
3. 3
   AutrePurification by silica gel (Merck KGaA, 230–400 mesh particle size) flash chromatography
4. 4
   Lavageeluting with chloroform

Mode opératoire

To a homogeneous solution of sodium thiocyanate (21 mg, 0.26 mmol) in ethyl acetate (1 mL), at room temperature under a nitrogen atmosphere, was added 4-fluorophenyl-acetyl chloride (28 μL, 0.20 mmol). The mixture was stirred for 30 minutes before being added directly to a homogeneous solution of 3-fluoro-4-(pyrrolo[2,1-f][1,2,4]-triazin-4-yloxy)benzenamine (37 mg, 0.15 mmol, Compound C of Example 22) in anhydrous dichloromethane (3 mL), under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 h before being concentrated in vacuo. Purification by silica gel (Merck KGaA, 230–400 mesh particle size) flash chromatography, eluting with chloroform, afforded the title compound (55 mg, 83%). 1H NMR (CDCl3) δ 12.41 (s, 1H), 8.50 (s, 1H), 7.97 (s, 1H), 7.92 (m, 1H), 7.81 (m, 1H), 7.42 (m, 1H), 7.35–725 (m, 3H), 7.17–7.10 (m, 2H), 705–7.02 (m, 1H), 6.85–6.90 (m, 1H), 3.72 (s, 2H); HRMS(ESI), 440.0993 (M+H)+ calc, 440.0988 (M+H)+ found.

Source