1,4-diphenyl-1H-imidazole → 2-(1,4-diphenyl-1H-imidazol-2-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

HRID 1428948ノート

反応式

HRID 1428948 の反応式
C([Li])CCC.[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26].[Cl-].[NH4+].[Na]>C1COCC1>[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:13]2[CH2:24][C:25]([N:27]2[CH2:28][CH2:29][N:30]([C:33]3[N:34]=[CH:35][CH:36]=[CH:37][N:38]=3)[CH2:31][CH2:32]2)=[O:26])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 109329801,4-diphenyl-1H-imidazoleHCID 636798462-Bromo-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanoneHCID 86657765Sodium ammonium chlorideHCID 178418339Butyllithium

生成物 1

HCID 715996902-(1,4-diphenyl-1H-imidazol-2-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone収率 6.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

0.5 mL butyllithium (1.6 mol/L in THF) was added to 0.15 g 1,4-diphenyl-1H-imidazole in 10 mL THF at −78° C. under argon. The reaction was stirred 40 min at −78° C. and 0.22 g 2-bromo-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanon was added to the reaction. After stirring 1 h at −78° C. the reaction was decomposed with saturated sodiumammoniumchloride solution. The mixture was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5) to yield 20 mg of the desired compound. Rt: 1.13 (method B), (M+H)+: 425

後処理

  1. stirringAfter stirring 1 h at −78° C. the reaction
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5)

出典と根拠

ORDレコード
ord-902ec9a6b65642d8829e509314723d0e
出典データセット
uspto-grants-2015_01
特許番号
US08937176B2

反応ノート

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