5-Chlorotetrazolo(1,5-a][1,7]naphthyridine → HCID 12015801, Verbindung

HRID 47462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47462
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[N:13][N:14]=[C:4]2[CH:3]=1>C(N)C(C)C>[CH3:10][CH:11]([CH3:2])[CH2:6][NH:5][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[N:13][N:14]=[C:4]2[CH:3]=1

Komponenten

3

Edukt 1

HCID 120158005-Chlorotetrazolo(1,5-a][1,7]naphthyridine

Produkt 1

HCID 12015801HCID 12015801, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6558IsobutylamineLösungsmittel

Versuchsvorschrift

A suspension of 5-chlorotetrazolo[1,5-a][1,7]naphthyridine (20 g) in isobutylamine (100 mL) was heated at reflux for several hours. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane, washed with water, dried over magnesium sulfate then concentrated under vacuum. The residue was recrystallized from toluene to give a material that was a mixture by thin layer chromatography. The material was purified by flash chromatography, silica gel eluting with dichloromethane, 5-20% ethyl acetate in dichloromethane, and 10% methanol in dichloromethane. The fractions with the slower moving material were concentrated to provide N5-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-5-amine as a solid, m.p. 220-221° C. Analysis: Calculated for C12H14N6: %C, 59.49; %H, 5.82; %N, 34.69. Found: %C, 59.35; %H, 5.89; %N, 34.88.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for several hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationthen concentrated under vacuum
  7. customThe residue was recrystallized from toluene
  8. customto give a material that
  9. customThe material was purified by flash chromatography, silica gel eluting with dichloromethane, 5-20% ethyl acetate in dichloromethane, and 10% methanol in dichloromethane
  10. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-eea8866fd18d45d58d22cbb5d154f69c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699878B2

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