N,N'-Dimethylethylenediamine → tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)Pyridine-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate

HRID 57965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57965
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[N:29]=[CH:28][C:27]2[CH:30]=[N:31][NH:32][C:26]=2[CH:25]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[Cl:23][C:24]1[N:29]=[CH:28][C:27]2[CH:30]=[N:31][N:32]([C:2]3[N:7]=[C:6]([N:8]4[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]4)[CH:5]=[CH:4][CH:3]=3)[C:26]=2[CH:25]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridineHCID 86707089HCID 86707089, Verbindung

Produkt 1

HCID 86707090tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)Pyridine-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (800 mg, 2.16 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (330 mg, 2.16 mmol) in 1,4-dioxane (25 mL) was added CuI (164 mg, 0.86 mmol), N1,N2-dimethylethane-1,2-diamine (240 mg, 2.7 mmol), and K2CO3 (894 mg, 6.48 mmol). The mixture was heated at 100° C., which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using DCM:MeOH (20:1˜10:1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate as yellow solid (671 mg, 70%). MS (ESI) m/z: 445 [M+H]+.

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. concentrationwas concentrated under reduced pressure
  3. customThe crude material was purified by silica gel chromatography
  4. washas eluting solvents

Quellen und Nachweise

ORD-Eintrag
ord-e49b144ac57e43fea3bb1b4cd48ce45d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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