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

HRID 1959717

반응식

HRID 1959717 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-65a0ff50833d44508c8434f8b444aa59
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410264B2

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