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Lithium Hydroxide → 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylic acid

HRID 595095
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인쇄 미리보기

반응식

HRID 595095 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[CH:22]=[CH:21][C:20]=2[C:19]=1[C:31]([O:33]C)=[O:32])(=[O:16])=[O:15])[CH3:2].[OH-].[Li+]>O1CCOCC1>[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[CH:22]=[CH:21][C:20]=2[C:19]=1[C:31]([OH:33])=[O:32])(=[O:15])=[O:16])[CH3:36]
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참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 86712812methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate2회

생성물 1

HCID 714667058-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylic acid수율 60.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 1, 0.075 g) and lithium hydroxide (3M aqueous solution, 2 mL) in dioxane (6 mL) was heated to 80° C. for 6 hours. The resultant mixture was cooled and concentrated in vacuo. The residue was acidified using formic acid and then concentrated in vacuo. The residue was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was triturated with methanol. The mixture was centrifuged and the supernatant was decanted twice. The resultant solid was dried in vacuo overnight to give 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylic acid (0.044 g) as a solid.

후처리

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was triturated with methanol
  8. customthe supernatant was decanted twice
  9. customThe resultant solid was dried in vacuo overnight

출처 및 근거

ORD 기록
ord-d3b258c043574974ae9dd093d5e19b88
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242997B2

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