1,3-Propanediamine, N1,N1,N3-trimethyl- → ethyl 6-[N-(3-dimethylaminopropyl)-methylamino]-3-pyridazinecarboxylate

HRID 131258

Reaktionsgleichung

Reaktionsgleichung von HRID 131258
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:20])[CH2:15][CH2:16][CH2:17][NH:18][CH3:19].[N-]=C=O>O1CCCC1>[CH3:13][N:14]([CH3:20])[CH2:15][CH2:16][CH2:17][N:18]([CH3:19])[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 105034IsocyanateHCID 10352425Ethyl 6-chloropyridazine-3-carboxylate

Produkt 1

HCID 69299702ethyl 6-[N-(3-dimethylaminopropyl)-methylamino]-3-pyridazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 6-chloropyridazine-3-carboxylate (37 mg) in tetrahydrofuran (1.5 mL) is added N,N,N′-trimethylpropane-1,3-diamine (46 mg) and the mixture is stirred at room temperature overnight. The reaction mixture is diluted with tetrahydrofuran (1.5 mL) and thereto is added MP-Isocyanate (polystyrene methylisocyanate, 1.43 mmol/g, 400 mg). The mixture is shaken at room temperature overnight. The reaction mixture is filtered to remove the resin and the filtrate is extracted with chloroform/methanol. The organic layer is concentrated to give crude ethyl 6-[N-(3-dimethylaminopropyl)-methylamino]-3-pyridazinecarboxylate. MS (ESI) m/z: 267 [M+H]+

Aufarbeitung

  1. stirringThe mixture is shaken at room temperature overnight
  2. filtrationThe reaction mixture is filtered
  3. customto remove the resin
  4. extractionthe filtrate is extracted with chloroform/methanol
  5. concentrationThe organic layer is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-683ff35f102a48fbba67ab4e3232da89
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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