5-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol → 9-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol

HRID 1788067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788067
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:16]=3)[N:11]3[N:33]=[N:34][N:35]=[C:10]3[NH:9]2)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[CH:16]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]3=[N:35][N:34]=[N:33][N:9]23)[CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 1363420815-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

Produkt 1

HCID 1354245029-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanolAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of intermediate 9 (0.0014 mol) in toluene (10 ml) was stirred and refluxed for 48 hours, then brought to room temperature and the solvent was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.1). The pure fractions were collected and the solvent was evaporated. The residue (0.4 g, 57%) was washed with diethyl ether. The precipitate was filtered off and dried under a vacuo, yielding 0.35 g (50%) of 9-(3-chlorophenyl)-α-(4-fluorophenyl)-4,9-dihydro-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol (compound 2), mp. 180° C.

Aufarbeitung

  1. temperaturerefluxed for 48 hours
  2. custombrought to room temperature
  3. customthe solvent was evaporated till dryness
  4. customThe solvent was evaporated till dryness
  5. customThe residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.1)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. washThe residue (0.4 g, 57%) was washed with diethyl ether
  9. filtrationThe precipitate was filtered off
  10. customdried under a vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62b1e8b94e0e40819a548a7747a6c92b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511138B2

Notizen zur Reaktion

Wird geladen…