Sodium Azide → 5-(3-chlorophenyl)-alpha-(4-fluorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

HRID 1788046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788046
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)([C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[OH:20])[CH:8]=3)[N:3]3[N:34]=[N:35][N:36]=[C:2]3[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 179761032-chloro-4-(3-chlorophenyl)-alpha-(4-fluorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanol

Produkt 1

HCID 688635845-(3-chlorophenyl)-alpha-(4-fluorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanolAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of intermediate 7 (0.0125 mol) and sodium azide (0.038 mol) in DMF (60 ml) was stirred at 90° C. for 2 hours, then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water, taken up in DCM, filtered, washed with diethyl ether and dried under a vacuo, yielding 3.5 g (58%) of intermediate 8. The filtrate was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH 95/5/0.1). The pure fractions were collected and the solvent was evaporated. The residue (0.9 g, 15%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.7 g (12%) of 5-(3-chlorophenyl)-α-(4-fluorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 8), mp. 200° C.

Aufarbeitung

  1. custombrought to room temperature
  2. stirringstirred
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. filtrationfiltered
  6. washwashed with diethyl ether
  7. customdried under a vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eecfee5fb078407e937e0238498d097c
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511138B2

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