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

HRID 1890953ノート

反応式

HRID 1890953 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8b1c83d2441548a4a4071675b832fe2b
出典データセット
uspto-grants-2013_08
特許番号
US08507489B2

反応ノート

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