Ethylenediamine → 6-[6-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-quinoline

HRID 1890953노트

반응식

HRID 1890953 반응식
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[N:28]=[CH:27][CH:26]=[CH:25]5)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[N:8]1.FC(F)(F)C(O)=O.C(N)CN>ClCCl.CO>[NH:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([S:21][C:22]4[CH:23]=[C:24]5[C:29](=[CH:30][CH:31]=4)[N:28]=[CH:27][CH:26]=[CH:25]5)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[N:8]1

참가 물질

6

반응물 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 689770066-{6-[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl}-quinoline

생성물 1

HCID 1359070146-[6-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl]-quinoline수율 53.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a solution of 6-{6-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl}-quinoline (150 mg, 0.32 mmol) in dichloromethane (8 mL) at 0° C. was added trifluoroacetic acid. After 3 hours the mixture was concentrated to dryness and taken Up in dichloromethane and neutralized via the addition of aqueous NaHCO3. To this emulsion was added a chloroform/methanol (95/5) mixture (20 mL) and brine (30 mL). The organic phase was separated and the organic phase filtered and the solid residue washed with water then Et2O and dried to return a yellow solid (64 mg). This solid was taken up in methanol (2 mL) to which ethylenediamine (1 mmol) was added and heated at 50° C. for 1 hour. The mixture was cooled to ambient temperature and the solid collected via filtration and dried to return title compound as a white solid (57 mg, 0.17 mmol, 53% yield).

후처리

  1. concentrationAfter 3 hours the mixture was concentrated to dryness
  2. additiontaken Up in dichloromethane and neutralized via the addition of aqueous NaHCO3
  3. additionTo this emulsion was added a chloroform/methanol (95/5) mixture (20 mL) and brine (30 mL)
  4. customThe organic phase was separated
  5. filtrationthe organic phase filtered
  6. washthe solid residue washed with water
  7. dry with materialEt2O and dried
  8. additionwas added
  9. temperatureThe mixture was cooled to ambient temperature
  10. filtrationthe solid collected via filtration
  11. customdried

출처 및 근거

ORD 기록
ord-8b1c83d2441548a4a4071675b832fe2b
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507489B2

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