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HRID 41571Erstellt: 24. Oktober 2026

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

https://huagongshe.com/de/reaction/41571

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPotassium Phosphate, TribasicHCID 62657—
Edukttrans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 2733821—
Edukt2-(3-Iodobenzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneHCID 67252042—
EduktHCID 178418936HCID 178418936—
KatalysatorCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
LösungsmittelDimethylformamideHCID 6228—
Produkt2-(3-(2H-1,2,3-triazol-2-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneHCID 5325978830,9%

Reaktionsbedingungen

Temperatur110 °C

Reaktionsschritte

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%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08530648B2
Quelldatensatzuspto-grants-2013_09
ORD IDord-ea0d1d88435b4ecf80e476d0423ae564
Quellennotizuspto-grants-2013_09