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Hydrochloric Acid → (Rac)-2-{4-[3-(1-quinolin-6-yl-ethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-ethanol

HRID 69218
ノート
印刷プレビュー

反応式

HRID 69218 の反応式
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([CH:24]([C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[N:32]=[CH:31][CH:30]=[CH:29]5)[CH3:25])=[CH:22][N:23]=3)[N:20]=2)[CH:12]=[N:11]1.C(Cl)Cl.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.O.CC#N>[N:32]1[C:33]2[C:28](=[CH:27][C:26]([CH:24]([C:21]3[N:19]4[N:20]=[C:15]([C:13]5[CH:12]=[N:11][N:10]([CH2:9][CH2:8][OH:7])[CH:14]=5)[CH:16]=[CH:17][C:18]4=[N:23][CH:22]=3)[CH3:25])=[CH:35][CH:34]=2)[CH:29]=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 68641062(Rac)-6-[1-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1h-pyrazol-4-yl}-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline

生成物 1

HCID 57917405(Rac)-2-{4-[3-(1-quinolin-6-yl-ethyl)-imidazo[1,2-b]pyridazin-6-yl]-pyrazol-1-yl}-ethanol

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒
HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

In a flask were introduced (rac)-6-[1-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline (Stage 177.1, 147 mg, 0.33 mmol) and DCM (4 mL), before adding dropwise HCl in dioxane (4 N, 0.248 mL). The RM was stirred at rt for 1 h and was then blown off with nitrogen. The residue was dissolved in water/CH3CN 1:1. The solution was basified with NaHCO3 (ca. 0.5 g) before being concentrated. The white suspension was filtered and the cake was washed with water, before being dried under vacuum. The crude was dissolved in MeOH/water and purified by preparative HPLC (H2O/CH3CN/TFA 1000:0:1 to 750:250:1 in 20 min.). Collected fractions containing the product were put together and basified with NaHCO3, before being concentrated. The resulting white suspension was filtered and the cake was washed with water, before being dried under high vacuum to give the title compound as a white solid (tR 1.83 min (conditions 8), MH+=360).

後処理

  1. concentrationbefore being concentrated
  2. filtrationThe white suspension was filtered
  3. washthe cake was washed with water
  4. custombefore being dried under vacuum
  5. dissolutionThe crude was dissolved in MeOH/water
  6. custompurified by preparative HPLC (H2O/CH3CN/TFA 1000:0:1 to 750:250:1 in 20 min.)
  7. additionCollected fractions containing the product
  8. concentrationbefore being concentrated
  9. filtrationThe resulting white suspension was filtered
  10. washthe cake was washed with water
  11. custombefore being dried under high vacuum

出典と根拠

ORDレコード
ord-76b3502bdd7841f48fa2c9df3669a44b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822468B2

反応ノート

読み込み中…

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