Formic Acid → HCID 56656136, compound

HRID 1778323Notes

Reaction equation

HRID 1778323 reaction equation
[CH2:1]([NH:3][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>O.O1CCOCC1.C(O)C>[CH2:1]([NH:3][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:15])=[O:16])[CH3:2]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68093200HCID 68093200, compound2×

Product 1

HCID 56656136HCID 56656136, compoundYield 21.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 46, 0.096 g) and lithium hydroxide monohydrate (0.168 g) in water (0.8 mL) and dioxane (3.2 mL), was sealed in a microwave vial and irradiated in the microwave at 135° C. for 45 minutes. After cooling, the mixture was diluted with ethanol, acidified with formic acid and evaporated to dryness. The residue was triturated with 10% methanol in DCM, filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with DMAW 350. The product was azeotroped with toluene and ethanol and the residue was triturated with ethyl acetate to give 7-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid (0.020 g) as a white solid.

Workup

  1. customwas sealed in a microwave vial
  2. customirradiated in the microwave at 135° C. for 45 minutes
  3. temperatureAfter cooling
  4. customevaporated to dryness
  5. customThe residue was triturated with 10% methanol in DCM
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness
  8. customThe residue was purified by chromatography on silica
  9. washeluting with DMAW 350
  10. customThe product was azeotroped with toluene and ethanol
  11. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-aba619231765496a8a4254e6983e149b
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…