Water → HCID 22285585、化合物

HRID 1062443ノート

反応式

HRID 1062443 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[C:29]1[N:30]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[CH:31]=[C:32]([C:34](OCC)=O)[N:33]=1.O>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([N:30]2[CH:31]=[C:32]([CH2:34][N:18]3[CH2:19][CH2:20][N:15]([C:12]4[CH:11]=[CH:10][C:9]([CH3:8])=[CH:14][CH:13]=4)[CH2:16][CH2:17]3)[N:33]=[C:29]2[C:23]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=2[Cl:21])=[CH:44][CH:43]=1

参加物

6

反応物 4

HCID 962WaterHCID 11463589ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylateHCID 21226445Aluminium lithium hydrideHCID 222855141-(4-Methylphenyl)piperazine monohydrochloride

生成物 1

HCID 22285585HCID 22285585、化合物収率 2.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of lithium aluminum hydride (21 mg, 0.54 mmol) in THF (2 mL), 1-(4-methylphenyl)piperazine hydrochloride (32 mg, 0.13 mmol) was added. After 10 minutes, a solution of ethyl 2-(2,4-dichlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (39 mg, 0.1 mmol) in THF (2 mL) was added dropwise. The reaction mixture was stirred for 10 minutes, and diluted by water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by HPLC (YMC-packed Pro C18 20×150 mm column, 10-90% CH3CN in H2O/TFA, 25 mL/min) to give the product 1-{[1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazol-4-yl]methyl}-4-(4-methylphenyl)-piperazine (1.4 mg, 2% yield): LC-MS m/z 511.1 (MH+), retention time 2.94 min (method 1). 1H NMR (300 MHz, CDCl3) δ: 2.29 (3H, s), 3.42-3.49 (8H, br), 4.39 (2H, s), 6.85-7.41 (11H, m), 7.54 (1H, s).

後処理

  1. additionwas added
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC (YMC-packed Pro C18 20×150 mm column, 10-90% CH3CN in H2O/TFA, 25 mL/min)

出典と根拠

ORDレコード
ord-8e0e02a126db44309d732372b093505c
出典データセット
uspto-grants-2005_11
特許番号
US06960601B2

反応ノート

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