Lithium hydroxide, monohydrate → 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylic acid

HRID 595097노트

반응식

HRID 595097 반응식
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[C:24]3=[CH:28][CH:29]=[N:30][N:23]3[CH2:22][CH2:21][C:20]=2[C:19]=1[C:31]([O:33]C)=[O:32])(=[O:16])=[O:15])[CH3:2].O.[OH-].[Li+]>O1CCOCC1.O>[CH2:35]([N:3]([CH2:1][CH3:2])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[C:24]3=[CH:28][CH:29]=[N:30][N:23]3[CH2:22][CH2:21][C:20]=2[C:19]=1[C:31]([OH:33])=[O:32])(=[O:15])=[O:16])[CH3:36]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712814methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate2회

생성물 1

HCID 714724968-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylic acid수율 36.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 20, 0.057 g) and lithium hydroxide monohydrate (0.090 g) in dioxane (4 mL) and water (1 mL) was heated to 80° C. for 32 hours. The resultant mixture was concentrated in vacuo and the residue was acidified with aqueous citric acid solution (10%) and extracted into DCM, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-15% to give 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-5,6-dihydropyrazolo[5,1-a]isoquinoline-7-carboxylic acid (0.020 g) as a white solid.

후처리

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. extractionextracted into DCM
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM with a gradient of 0-15%

출처 및 근거

ORD 기록
ord-31d68ea23d1d4f6883fe63f2afe06828
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242997B2

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