Piperazine → 2-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)Pyrazine

HRID 2182141

반응식

HRID 2182141 반응식
Cl[C:2]1[N:7]=[C:6]([O: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]([O: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

참가 물질

7

반응물 4

HCID 4837PiperazineHCID 634876Binap, (A+-)-HCID 224819733-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrileHCID 23676156Sodium t-butoxide

생성물 1

HCID 98573352-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)Pyrazine수율 22.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-(6-chloro-pyrazin-2-yloxymethyl)-benzonitrile I-3f (667.2 mg, 2.716 mmol), piperazine (297 mg, 3.531 mmol), sodium t-butoxide (287 mg, 2.987 mmol), BINAP (67.7 mg, 0.109 mmol), and Pd2(dba)3 (49.7 mg, 0.054 mmol) in toluene (10 mL) was heated at 90° C. overnight. 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. The product was purified by chromatography (silica, 10% MeOH/dichlormethane with 1% NH4OH) to give 180 mg 3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-yloxymethyl)-benzonitrile (3-E).

후처리

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. washThe celite pad was washed with ethyl acetate several times
  4. concentrationThe combined filtrate was concentrated in vacuo
  5. customto give the crude title compound
  6. customThe product was purified by chromatography (silica, 10% MeOH/dichlormethane with 1% NH4OH)

출처 및 근거

ORD 기록
ord-e6a659b29715454186b3e8c2350cf27b
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894050B2

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