Réaction #69849

Équation de réaction

2-(3-iodobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

1H-1,2,3-triazole

trans-N,N′-dimethylcyclohexane-1,2-diamine

K3PO4

→

title compounds

Rendement 30.9%

2-(3-(2H-1,2,3-triazol-2-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

Rendement 30.9%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe reaction mixture was cooled to it
3. 3
   Filtrationfiltered
4. 4
   Autreto remove the solids
5. 5
   ConcentrationThe filtrate was concentrated under reduced pressure
6. 6
   AutreThe residue was purified by reversed phase preparative HPLC (column AG/PP/C-18-15/025, flow 20 mL/min, mobile phase water (A): acetonitrile (B) gradient)

Mode opératoire

To a mixture of 2-(3-iodobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (104 mg, 0.20 mmol), 1H-1,2,3-triazole (28 mg, 0.40 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (6 mg, 0.04 mmol) and K3PO4 (127 mg, 0.60 mmol) in DMF (2 mL), CuI (15 mg, 0.08 mmol) was added and the reaction mixture was stirred at 110° C. for 24 h. The reaction mixture was cooled to it and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by reversed phase preparative HPLC (column AG/PP/C-18-15/025, flow 20 mL/min, mobile phase water (A): acetonitrile (B) gradient) to yield the regioisomeric title compounds (example 8: 28 mg, 31% and example 9: 54 mg, 60%).

Source