Ammonium formate → methyl 7-(2,2-dimethylpropionylamino)-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate

HRID 2200338Notes

Reaction equation

HRID 2200338 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]2[CH2:6][O:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=3[C:23]([O:25][CH3:26])=[O:24].C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:19][C:18]([CH3:21])([CH3:20])[C:17]([NH:16][C:10]1[C:9]([C:23]([O:25][CH3:26])=[O:24])=[C:8]2[C:13]([C:14]3[CH:15]=[CH:2][N:3]=[N:4][C:5]=3[CH2:6][O:7]2)=[CH:12][CH:11]=1)=[O:22]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89705413methyl 3-chloro-7-(2,2-dimethylpropionylamino)-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate2×

Product 1

HCID 89705397methyl 7-(2,2-dimethylpropionylamino)-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylateYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of methyl 3-chloro-7-(2,2-dimethylpropionylamino)-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate (Intermediate 8, 1.01 g), ammonium formate (0.848 g) and 10% palladium on carbon (0.150 g) in ethanol (60 mL) was stirred and heated at reflux under nitrogen for one hour. After cooling, the suspension was filtered and the filtrate was evaporated. The residue was dissolved in ethyl acetate and washed with water (with warming to dissolve all of the solid), dried (Na2SO4) and filtered. The filtrate was evaporated in vacuo and the residue was triturated with ether. The solid was collected by filtration and purified by chromatography on silica, eluting with ethyl acetate to give methyl 7-(2,2-dimethylpropionylamino)-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate (0.705 g) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for one hour
  3. temperatureAfter cooling
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water (
  8. temperaturewith warming
  9. dissolutionto dissolve all of the solid),
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customThe filtrate was evaporated in vacuo
  13. customthe residue was triturated with ether
  14. filtrationThe solid was collected by filtration
  15. custompurified by chromatography on silica
  16. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d320e540801649d387706ef2035d0c7d
Source dataset
uspto-grants-2016_06
Patent number
US09359369B2

Reaction notes

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