Ammonium Chloride → 7-[2-(3-Diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acid

HRID 1778326Notes

Reaction equation

HRID 1778326 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[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]C)=[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].O.[OH-].[Li+].[Cl-].[NH4+]>O1CCOCC1.O>[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]([OH:30])=[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

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 66685060Methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 566562807-[2-(3-Diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acidYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-furo[2,3-c]quinoline-6-carboxylate (Intermediate 71, 0.100 g) and lithium hydroxide monohydrate (0.250 g) in dioxane (4 mL) and water (1.25 mL) was heated at 80° C. overnight. The mixture was cooled and saturated aqueous ammonium chloride was added. This was concentrated in vacuo and the residue was triturated with DCM and methanol, filtered and the filtrate was concentrated in vacuo. The residue was purified by HPLC (C6 Ph) eluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 10-40% to give a yellow gum. The product was triturated with ether to give 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonyl-amino]-furo[2,3-c]quinoline-6-carboxylic acid (0.045 g) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationThis was concentrated in vacuo
  3. customthe residue was triturated with DCM and methanol
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by HPLC (C6 Ph)
  7. washeluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 10-40%
  8. customto give a yellow gum
  9. customThe product was triturated with ether

Sources & evidence

ORD record
ord-d4cff78819d04bbcbb38cf2bb42ab2ed
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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