2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 8-Chloro-2-methyl-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine

HRID 236726

Reaktionsgleichung

Reaktionsgleichung von HRID 236726
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH3:15])[CH:14]=[C:10]3[C:9](=O)[NH:8][CH:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH3:15])[CH:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 123778928-Chloro-2-methyl-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine

Produkt 1

HCID 123778938-Chloro-2-methyl-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2.52 g. (7.8 mmol) of the end product of Example 16 in 75 ml. dry THF was reduced with 3.12 ml. (31.2 mmol) of BMS according to the procedure described above in 6, Method B. The crude product from this reduction was then treated with 2.15 g. (9.4 mmol) of DDQ according to the oxidation procedure described above in Example 8. The crude oxidation product was chromatographed on a 29×20 cm column of silica gel packed in benzene and eluted first with 3% EtOAc in benzene and then 5% EtOAc in benzene. Recrystallization from CH3OH/H2O of the material isolated from the column yielded the analytically pure end product as colorless needles: mp 105°-107°.

Aufarbeitung

  1. customThe crude oxidation product was chromatographed on a 29×20 cm column of silica gel
  2. washeluted first with 3% EtOAc in benzene
  3. customRecrystallization from CH3OH/H2O of the material
  4. customisolated from the column
  5. customyielded the analytically pure end product as colorless needles

Quellen und Nachweise

ORD-Eintrag
ord-79e4d72ea5f54858a66a748fd6b6ba41
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157331

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