Hydrochloric Acid → 1-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1892378ノート

反応式

HRID 1892378 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>CO>[N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH2:15][C:12]3[N:10]4[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]4=[N:14][N:13]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 698109446-((6-(1-Ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

生成物 1

HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone収率 51.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-((6-(1-ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline in MeOH (30 mL) was added excess 3N HCl solution. The solution was stirred at rt overnight and neutralized with saturated NaHCO3 solution. Organic solvent was evaporated and the residue was extracted with EtOAc three times. Organic layers were combined, washed with brine and dried over Na2SO4. Solvent was evaporated and the crude was purified by column chromatography (DCM:MeOH=95:5) to give the title compound as yellow solid (51.3%). LCMS (method B): [MH]+=304.1, tR=1.708 min.

後処理

  1. customOrganic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customthe crude was purified by column chromatography (DCM:MeOH=95:5)

出典と根拠

ORDレコード
ord-120df94ca1a6475b9dcd57d6034c247b
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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