N-BOC-ethylenediamine → HCID 86587464, compound

HRID 897313Notes

Reaction equation

HRID 897313 reaction equation
Br[C:2]1[N:11]=[C:10](C(NCC2C=CC(F)=CC=2)=O)[C:9](O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(C([Sn])=C(CCCC)CCCC)CCC.[C:39]([NH:46]CCN)([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:39]([NH:46][N:7]1[C:2]2[C:3](=[CH:8][CH:9]=[CH:10][N:11]=2)[CH:4]=[CH:5][CH2:6]1)([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

Participants

6

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 86587464HCID 86587464, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-[1,6]naphthyridine-7-carboxamide (2.00 g, 5.33 mmol), tri-n-butylvinyl tin (3.12 mL, 10.70 mmol), bis (triphenylphosphine)palladium(II) chloride (0.75 g, 1.10 mmol), N-Boc-ethylenediamine (4.23 g, 26.6 mmol) in dioxane (50 mL) was purged with nitrogen and heated with stirring at 100° C. in a sealed tube overnight. The resultant product mixture was filtered through a pad of Celite. The filtrate was 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 N-Boc amino napthyridine.

Workup

  1. customwas purged with nitrogen
  2. temperatureheated
  3. filtrationThe resultant product mixture was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated under vacuum
  5. dissolutionThe residue was dissolved in DMSO
  6. customsubjected to HPLC purification on C-18 stationary phase
  7. washeluted with water/acetonitrile/TFA mobile phase
  8. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-2bb9974aaf434529984fa2460dd7142d
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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