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

HRID 595095Notes

Reaction equation

HRID 595095 reaction equation
[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]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86712812methyl 8-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d3b258c043574974ae9dd093d5e19b88
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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