3,5-Difluorobenzaldehyde 2-(6-chloro-5-cyclobutyl-3-pyridazinyl)hydrazone → 6-Chloro-7-cyclobutyl-3-(3,5-difluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 2306581노트

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HRID 2306581 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][N:9]=[CH:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[CH:4][C:3]=1[CH:19]1[CH2:22][CH2:21][CH2:20]1>C(O)C>[Cl:1][C:2]1[C:3]([CH:19]2[CH2:20][CH2:21][CH2:22]2)=[CH:4][C:5]2[N:6]([C:10]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=3)=[N:9][N:8]=2)[N:7]=1

참가 물질

3

반응물 1

HCID 739859023,5-Difluorobenzaldehyde 2-(6-chloro-5-cyclobutyl-3-pyridazinyl)hydrazone

생성물 1

HCID 226098996-Chloro-7-cyclobutyl-3-(3,5-difluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine수율 63%

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
70 °C

실험 절차

Ferric chloride (3.423 g, 12.66 mmol) in ethanol (15 ml) was added dropwise to a solution of N-(6-chloro-5-cyclobutylpyridazin-3-yl)-N′-(3,5-difluorobenzylidene)hydrazine (0.816 g, 2.53 mmol) in ethanol (35 ml) and heated at 70° C. After 3 hours the reaction mixture was partitioned between dichloromethane (250 ml) and brine (250 ml). The organic phase was dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate-hexane mixtures to afford the title pyridazine (0.51 g, 63%). 1H NMR (250 MHz, CDCl3) 1.84-2.08 (1H, m), 2.08-2.36 (3H, m), 2.42-2.68 (2H, m), 3.65-3.87 (1H, m), 6.88-7.06 (1H, m), 8.01 (1H, s), 8.04-8.21 (2H, m). MS (ES+) 321 [MH]+, 323 [MH]+.

후처리

  1. customAfter 3 hours the reaction mixture was partitioned between dichloromethane (250 ml) and brine (250 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with ethyl acetate-hexane mixtures

출처 및 근거

ORD 기록
ord-e4acd3c4475b40a08eeee5c1dfc691c7
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828322B2

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