Formic Acid → HCID 56656210, compound

HRID 1778325Notes

Reaction equation

HRID 1778325 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([C:22]([O:24]C)=[O:23])=[C:20]3[C:15]([C:16]4[CH:28]=[CH:27][O:26][C:17]=4[CH2:18][O:19]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[C:4](/[CH:29]=[CH:30]\[CH2:31][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:3]=1.O.[OH-].[Li+].C(O)=O>O.O1CCOCC1.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([C:22]([OH:24])=[O:23])=[C:20]3[C:15]([C:16]4[CH:28]=[CH:27][O:26][C:17]=4[CH2:18][O:19]3)=[CH:14][CH:13]=2)(=[O:9])=[O:10])=[C:4](/[CH:29]=[CH:30]\[CH2:31][N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[CH:3]=1

Participants

7

Reactant 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 68093248HCID 68093248, compound2×

Product 1

HCID 56656210HCID 56656210, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 7-{4-fluoro-2-[(Z)-3-(morpholin-4-yl)prop-1-enyl]-benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 51, 0.408 g) and lithium hydroxide monohydrate (0.526 g) in water (2.5 mL) and dioxane (10 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 and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with DMAW 350. The resultant product was azeotroped with toluene and ethanol to give a solid which was triturated with methanol. The solid was collected by filtration and purified by chromatography on silica, eluting with methanol and DCM, with a gradient of 0-10%. The resultant product was triturated with acetone the solid was collected by filtration to give 7-{4-fluoro-2-[(Z)-3-(morpholin-4-yl)prop-1-enyl]benzenesulfonylamino}-4H-furo[2,3-c]chromene-6-carboxylic acid (0.155 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 resultant product was azeotroped with toluene and ethanol
  11. customto give a solid which
  12. customwas triturated with methanol
  13. filtrationThe solid was collected by filtration
  14. custompurified by chromatography on silica
  15. washeluting with methanol and DCM, with a gradient of 0-10%
  16. customThe resultant product was triturated with acetone the solid
  17. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-bbd8d93f6f264a43a6737c773a6a575c
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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