Piperazin-2-one → HCID 22346280, compound

HRID 897312Notes

Reaction equation

HRID 897312 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.C(C([Sn])=C(CC[CH2:36][CH3:37])CCCC)CCC.[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][C:40]1=[O:45]>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>[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]([CH2:44][CH2:43][N:42]3[CH2:37][CH2:36][NH:39][C:40](=[O:45])[CH2:41]3)[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 231360Piperazin-2-oneHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamideHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 22346280HCID 22346280, 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 (0.40 g, 1.06 mmol), tri-n-butylvinyl tin (0.62 mL, 2.13 mmol), bis (triphenylphosphine)palladium(II) chloride (0.15 g, 0.21 mmol), 2-piperazinone (0.12 g, 1.17 mmol) in dioxane (10 mL) was purged with nitrogen and heated with stirring at 100° C. in a sealed tube for 24 hours. 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 compound as yellow solid.

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-d825dfbcf7ba454c88ae7d4c8a7e6c39
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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