Hydrochloric Acid → 1-(3-(1-(5,7-Difluoroquinolin-6-yl)ethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1892401ノート

反応式

HRID 1892401 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH:15]([C:17]3[C:18]([F:28])=[C:19]4[C:24](=[CH:25][C:26]=3[F:27])[N:23]=[CH:22][CH:21]=[CH:20]4)[CH3:16])=[N:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl>CC(O)=O>[F:28][C:18]1[C:17]([CH:15]([C:12]2[N:10]3[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]3=[N:14][N:13]=2)[CH3:16])=[C:26]([F:27])[CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 581905356-{1-[6-(1-Ethoxy-vinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]-ethyl}-5,7-difluoro-quinoline

生成物 1

HCID 581904661-(3-(1-(5,7-Difluoroquinolin-6-yl)ethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

The crude 6-{1-[6-(1-ethoxy-vinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]-ethyl}-5,7-difluoro-quinoline obtained from the previous step was dissolved in HOAc (50 mL), 3N HCl aqueous solution (5 mL) was added. The reaction mixture was stirred at rt overnight. LC/MS showed the reaction was complete. Solvent was removed under reduced pressure. EtOAc was added, and cold 1N NaOH aqueous solution was added slowly until pH 8-9. The mixture was extracted with EtOAc, and the combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and purified by column chromatography to afford 1.0 g (65% for two steps) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.92 (dd, 1H), 8.32 (d, 1H), 8.14 (d, 1H), 7.68 (d, 1H), 7.61 (d, 1H), 7.42 (dd, 1H), 5.32 (q, 1H), 2.43 (s, 3H), 2.21 (d, 3H). LCMS (method A): [MH]+=354, tR=4.42 min.

後処理

  1. customSolvent was removed under reduced pressure
  2. additionEtOAc was added
  3. additioncold 1N NaOH aqueous solution was added slowly until pH 8-9
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

出典と根拠

ORDレコード
ord-e209ee3e364e449eb2c9979b88f8e758
出典データセット
uspto-grants-2013_08
特許番号
US08507676B2

反応ノート

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