Ethylenediaminetetraacetic Acid → HCID 20816879, compound

HRID 897336Notes

Reaction equation

HRID 897336 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[S:24]1(=[O:33])(=[O:32])[CH2:30][CH2:29][NH:28][C:27](=[O:31])[CH2:26][NH:25]1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[Na][Na]>N1C=CC=CC=1.[Cu-]=O.C(Cl)(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([N:25]3[CH2:26][C:27](=[O:31])[NH:28][CH2:29][CH2:30][S:24]3(=[O:33])=[O:32])[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 141233DisodiumHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 22346408HCID 22346408, compound

Product 1

HCID 20816879HCID 20816879, compound

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy[1,6]naphthyridine-7-carboxamide (0.99 g, 2.66 mmol), 1,2,5-thiadiazepan-4-one 1,1-dioxide from step 2 (0.41 g, 2.5 mmol) and copper (I) oxide (0.18 g, 1.25 mmol) in pyridine (13 mL) was heated in an oil bath at 115° C. overnight. The resultant mixture was treated with a mixture of chloroform (200 mL) and a saturated aqueous solution of ethylenediamine tetraacetic acid, disodium salt (200 mL) and stirred vigorously at room temp overnight in the presence of air. The slurry was filtered through a pad of Celite. The organic extract was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. filtrationThe slurry was filtered through a pad of Celite
  2. extractionThe organic extract
  3. customwas separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue was dissolved in DMSO
  8. customsubjected to HPLC purification on C-18 stationary phase
  9. washeluted with water/acetonitrile/TFA mobile phase
  10. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-e0e29a9bc6604ec49c54c0a74c8301aa
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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