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

HRID 2182141

反応式

HRID 2182141 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e6a659b29715454186b3e8c2350cf27b
出典データセット
uspto-grants-2005_05
特許番号
US06894050B2

関連ノート

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