6-Chloro-N-methyl-3-pyridinemethanamine → iso-Propyl 4-acetoxy-3-[(6-chloropyrid-3-ylmethyl)amino]but-2-enecarboxylate

HRID 1797837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797837
[C:1]([O:4][CH2:5][C:6]#[C:7][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])(=[O:3])[CH3:2].[Cl:15][C:16]1[N:21]=[CH:20][C:19]([CH2:22][NH:23]C)=[CH:18][CH:17]=1>O1CCCC1>[C:1]([O:4][CH2:5][C:6]([NH:23][CH2:22][C:19]1[CH:20]=[N:21][C:16]([Cl:15])=[CH:17][CH:18]=1)=[CH:7][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 86649326Iso-propyl 4-acetoxybut-2-ynecarboxylate

Produkt 1

HCID 86649325iso-Propyl 4-acetoxy-3-[(6-chloropyrid-3-ylmethyl)amino]but-2-enecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To an initial charge of 124 mg (0.672 mmol) of iso-propyl 4-acetoxybut-2-ynecarboxylate in 5 ml of anhydrous tetrahydrofuran (THF) are added dropwise 116 mg (0.739 mmol) of 1-(6-chloropyridin-3-yl)-N-methylmethanamine, dissolved in 1 ml of anhydrous THF, at room temperature. The reaction mixture is stirred at room temperature for 16 h and concentrated under reduced pressure. Subsequently, the residue is taken up with toluene and washed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution. After drying over magnesium sulphate and concentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate are obtained.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. washwashed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution
  3. dry with materialAfter drying over magnesium sulphate
  4. concentrationconcentrating the organic phase under reduced pressure, 120 mg (50% of theory) of iso-propyl 4-acetoxy-3-[(4-chlorobenzyl)(methyl)amino]but-2-enecarboxylate
  5. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-a49d1405dfc24e3f89814c4ad6668d7b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343893B2

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