1,3,5-Triazine → Rizatriptan

HRID 507370

Reaktionsgleichung

Reaktionsgleichung von HRID 507370
[NH:1]([CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[NH2:2].[N:18]1[CH:23]=NC=N[CH:19]=1>C(O)C.C(OC)(C)(C)C>[CH3:17][N:15]([CH2:14][CH2:13][C:7]1[C:6]2[CH:5]=[C:4]([CH2:3][N:1]3[N:2]=[CH:23][N:18]=[CH:19]3)[CH:12]=[CH:11][C:10]=2[NH:9][CH:8]=1)[CH3:16]

Komponenten

5

Edukt 2

HCID 92621,3,5-TriazineHCID 11492361[2-(5-Hydrazinomethyl-1H-indol-3-yl)-ethyl]-dimethyl-amine

Produkt 1

HCID 5078RizatriptanAusbeute 157,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

A solution of [2-(5-Hydrazinomethyl-1H-indol-3-yl)-ethyl]-dimethyl-amine (3.1 g, 85% purity, 11.9 mmol) and 1,3,5-triazine (0.69 g, 8.5 mmol) in ethanol (50 ml) is refluxed over night. The solution is then diluted with tert-butyl methylether (TBME), and the precipitated ammonium salts are filtered off. Removal of the solvent on the rotavapor produces 3.6 g of an oil which is chromatographed on silica (CH2Cl2: MeOH:NH4OH 98:2:1 to 95:5:1 v:v:v) to give 1.75 g (55%) of the product, dimethyl-[2-(5-[1,2,4]triazol-1-ylmethyl-1H-indol-3-yl)-ethyl]amine (Rizatriptan). HPLC retention time: 4.0 min.

Aufarbeitung

  1. filtrationthe precipitated ammonium salts are filtered off
  2. customRemoval of the solvent on the rotavapor

Quellen und Nachweise

ORD-Eintrag
ord-245658f4d9f94069a41734dc66a35325
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786156B2

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