Water → 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylic acid

HRID 2200331Notes

Reaction equation

HRID 2200331 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[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:31]([C:32]([O:34]C)=[O:33])=[C:30]2[C:21]([C:22]3[CH:23]=[CH:24][N:25]=[N:26][C:27]=3[CH2:28][O:29]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].O.[OH-].[Li+].O1CCOCC1.O>CO.CC(C)=O.C(O)=O>[CH2:36]([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:31]([C:32]([OH:34])=[O:33])=[C:30]2[C:21]([C:22]3[CH:23]=[CH:24][N:25]=[N:26][C:27]=3[CH2:28][O:29]2)=[CH:20][CH:19]=1)(=[O:15])=[O:16])[CH3:37]

Participants

8

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 89705427methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate2×

Product 1

HCID 897055067-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate (Intermediate 1, 0.249 g), lithium hydroxide monohydrate (0.474 g), dioxan (9 mL) and water (2.25 mL) was irradiated in the microwave at 135° C. for 45 minutes. The resulting solution was diluted with methanol, acidified with formic acid and evaporated in vacuo. The residue was dissolved in ethanol and toluene and evaporated in vacuo. The residue was triturated with 20% methanol in dichloromethane and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-30% to give a gum which was dissolved in acetone. A solid precipitated out on standing. This was collected by filtration to give 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylic acid (0.178 g) as a white solid.

Workup

  1. customwas irradiated in the microwave at 135° C. for 45 minutes
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethanol
  4. customtoluene and evaporated in vacuo
  5. customThe residue was triturated with 20% methanol in dichloromethane
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of methanol and DCM with a gradient of 0-30%
  10. customto give a gum which
  11. customA solid precipitated out
  12. filtrationThis was collected by filtration

Sources & evidence

ORD record
ord-2f07d5300be7442e905b2813938bca55
Source dataset
uspto-grants-2016_06
Patent number
US09359369B2

Reaction notes

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