methyl 7-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate → Methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate

HRID 1778389Notes

Reaction equation

HRID 1778389 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[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]2[C:21]([C:22]3[CH:34]=[CH:33][O:32][C:23]=3[CH:24]=[N:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2]>C(O)(=O)C.O1CCOCC1.[OH-].[OH-].[Pd+2]>[CH2:35]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]2[C:21]([C:22]3[CH:34]=[CH:33][O:32][C:23]=3[CH:24]=[N:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:36]

Participants

5

Reactant 1

HCID 68093355methyl 7-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 66685060Methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylateYield 55.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate (Intermediate 6, 0.180 g) and palladium hydroxide on carbon (˜0.005 g) in acetic acid (2 mL) and dioxane (20 mL) was stirred at room temperature under an atmosphere of hydrogen for 2 hours. The resultant mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated in vacuo to give methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate (0.100 g) as a gum which was used without further characterisation.

Workup

  1. filtrationThe resultant mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a4fbd5381f504f909723569c98feda4e
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…