Piperazine → HCID 9943968, compound

HRID 2182172Notes

Reaction equation

HRID 2182172 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[CH:5]=[N:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:18]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[C:13]#[N:14])[N:7]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 634876Binap, (A+-)-HCID 224820193-[[(6-Chloro-2-pyrazinyl)amino]methyl]benzonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 9943968HCID 9943968, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-[(6-chloro-pyrazin-2-ylamino)-methyl]-benzonitrile I-4n (37.6 mg, 0.154 mmol), piperazine (16 mg, 0.185 mmol), sodium t-butoxide (18 mg, 0.185 mmol), BINAP (3.8 mg, 0.006 mmol), and Pd2(dba)3 (2.8 mg, 0.003 mmol) in toluene (2 mL) was heated at reflux under nitrogen for 10 h. The solution was cooled to room temperature and filtered through a celite pad. The celite pad was washed with ethyl acetate several times. The combined filtrate was concentrated in vacuo to give the crude title compound 4-S. The product was purified by chromatography (silica, 10% MeOH/dichlormethane with 1% NH4OH) to give the title compound 4-S (10 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 10 h
  3. filtrationfiltered through a celite pad
  4. washThe celite pad was washed with ethyl acetate several times
  5. concentrationThe combined filtrate was concentrated in vacuo
  6. customto give the crude title compound 4-S
  7. customThe product was purified by chromatography (silica, 10% MeOH/dichlormethane with 1% NH4OH)

Sources & evidence

ORD record
ord-0e7817220f4c4cd58da69a89f955d242
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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