Formic Acid → HCID 56656141, compound

HRID 1778322Notes

Reaction equation

HRID 1778322 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[CH2:24][O:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].[OH-].[Li+].C(O)=O>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[CH2:24][O:25]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:36]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 3939Lithium HydroxideHCID 66685618HCID 66685618, compound2×

Product 1

HCID 56656141HCID 56656141, compoundYield 19.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 45, 0.130 g) and lithium hydroxide (0.105 g) in dioxane (3 mL) and water (1 mL) was heated at 90° C. for 20 hours. After cooling, the mixture was diluted with water (20 mL) and acidified to pH5-6 with formic acid. This was extracted into ethyl acetate. The combined organic layers were dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 0-10%. The product was triturated with diethyl ether/ethyl acetate (1:1) to give 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid (0.025 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionThis was extracted into ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM, with a gradient of 0-10%
  8. customThe product was triturated with diethyl ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-e81852616ae54289840f31ad024c9009
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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