Formic Acid → 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylic acid

HRID 1778321Notes

Reaction equation

HRID 1778321 reaction equation
O.[OH-].[Li+].[CH2:4]([N:6]([CH2:38][CH3:39])[CH2:7]/[CH:8]=[CH:9]\[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[S:17]([NH:20][C:21]1[C:30]([C:31]([O:33]C)=[O:32])=[C:29]2[C:24]([C:25]3[CH:37]=[CH:36][O:35][C:26]=3[CH:27]=[N:28]2)=[CH:23][CH:22]=1)(=[O:19])=[O:18])[CH3:5].C(O)=O>O1CCOCC1.O>[CH2:38]([N:6]([CH2:4][CH3:5])[CH2:7]/[CH:8]=[CH:9]\[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[S:17]([NH:20][C:21]1[C:30]([C:31]([OH:33])=[O:32])=[C:29]2[C:24]([C:25]3[CH:37]=[CH:36][O:35][C:26]=3[CH:27]=[N:28]2)=[CH:23][CH:22]=1)(=[O:19])=[O:18])[CH3:39]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68093355methyl 7-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 566561407-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylic acidYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Lithium hydroxide monohydrate (0.107 g) was added to a solution of methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]-quinoline-6-carboxylate (Intermediate 6, 0.026 g) in a mixture of dioxane (1.7 mL) and water (0.8 mL). The resultant mixture was stirred and heated at 90° C. overnight. After cooling, the mixture was acidified by addition of formic acid and then evaporated to dryness. The residue was triturated with a mixture of methanol and DCM (10%) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-12%. The product was triturated with a mixture of DCM and diethyl ether (50%) and the solid was collected by filtration and dried in vacuo to give 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylic acid (0.013 g) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customevaporated to dryness
  3. customThe residue was triturated with a mixture of methanol and DCM (10%)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM with a gradient of 0-12%
  8. customThe product was triturated with a mixture of DCM and diethyl ether (50%)
  9. filtrationthe solid was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0a46d1651e1b43f3a19ed92bb14fa852
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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