3,4-Dimethoxy-1,2,5-thiadiazole 1-oxide → 3-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide

HRID 235665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235665
[CH3:1][O:2][C:3]1[C:7](OC)=[N:6][S:5](=[O:10])[N:4]=1.[NH2:11][C:12]1[C:13]([CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1>CO>[NH2:11][C:12]1[C:13]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:7]2[C:3]([O:2][CH3:1])=[N:4][S:5](=[O:10])[N:6]=2)=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1

Komponenten

4

Edukt 2

HCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 145374593-Amino-5-bromo-(4-aminobutyl)pyridine

Produkt 1

HCID 159623603-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.995 g) in methanol (25 ml) was reacted with a solution of 3-amino-5-bromo-(4-aminobutyl)pyridine (1.5 g) in methanol (25 ml) at room temperature for 3 hours. The solvent was removed in vacuo and the residue was chromatographed on silica in ethanol to give an oil which was triturated with ether and recrystallised from ethanol/ether to give 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide (1.7 g) m.p. 118°-120° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica in ethanol
  3. customto give an oil which
  4. customwas triturated with ether
  5. customrecrystallised from ethanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-d0ed4aac0ba54e368c62f1546ad33f29
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640926

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