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

HRID 66236

반응식

HRID 66236 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-37ac342721a2430aa03c43144fd54248
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04130716

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