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

HRID 57844

Reaktionsgleichung

Reaktionsgleichung von HRID 57844
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][NH:31][C:25]=2[CH:24]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Cl:22][C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][N:31]([C:2]3[N:7]=[C:6]([N:8]4[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]4)[CH:5]=[CH:4][CH:3]=3)[C:25]=2[CH:24]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridineHCID 70700340tert-Butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate

Produkt 1

HCID 86707047tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylateAusbeute 57,3 %

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)-1,4-diazepane-1-carboxylate (2.55 g, 7.16 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (1.0 g, 6.51 mmol) in 1,4-dioxane (20 mL) was added CuI (494 mg, 2.6 mmol), K2CO3 (3.6 g, 26 mmol), and N1,N2-dimethylethane-1,2-diamine (460 mg, 5.2 mmol). The mixture was heated at 100° C. for 3 hours, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a yellow solid (1.6 g, 57%). MS (ESI) m/z: 429 [M+H]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1943d0852c264f4d8db42f973130b916
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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