Formic Acid → HCID 56656401, compound

HRID 1778330Notes

Reaction equation

HRID 1778330 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]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].O.[OH-].[Li+].C(O)=O>O1CCOCC1.O.C(Cl)Cl>[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[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

7

Reactant 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86684725Methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate2×

Product 1

HCID 56656401HCID 56656401, compoundYield 7.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 4, 1.73 g) and lithium hydroxide monohydrate (1.41 g) in dioxane (27 mL) and water (9 mL) was heated to 100° C. for 16 hours, under an atmosphere of nitrogen. The mixture was cooled to room temperature and diluted with DCM (100 mL) and water (100 mL). This mixture was acidified to pH6 using formic acid and the layers were separated. The aqueous layer was extracted with a further 3×100 mL DCM. The combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give a tan solid. This was purified by chromatography on silica, eluting with a mixture of 2M ammonia solution in methanol and DCM with a gradient of 10-20% to give 7-[2-((E)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-4H-furo[2,3-c]chromene-6-carboxylic acid (0.133 g), isolated as the minor by-product of the reaction.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with a further 3×100 mL DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give a tan solid
  9. customThis was purified by chromatography on silica
  10. washeluting with a mixture of 2M ammonia solution in methanol and DCM with a gradient of 10-20%

Sources & evidence

ORD record
ord-0a2844425cd5446da1c4f9855e62f26a
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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