Methanol → (4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one

HRID 645723

反応式

HRID 645723 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20](Cl)=[O:21])[C:10]([C:23]3[C:24]([O:29][CH2:30][CH3:31])=[N:25][CH:26]=[CH:27][CH:28]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][C:40]1=[O:45].CO>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:20]([N:39]3[CH2:44][CH2:43][NH:42][CH2:41][C:40]3=[O:45])=[O:21])[C:10]([C:23]3[C:24]([O:29][CH2:30][CH3:31])=[N:25][CH:26]=[CH:27][CH:28]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 887MethanolHCID 8471TriethylamineHCID 231360Piperazin-2-oneHCID 866136224,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

生成物 1

HCID 86613623(4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one収率 86.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl chloride (100 mg, 0.211 mmol) in methylene chloride (3 mL) at room temperature were added triethylamine (88 uL) and 2-piperazinone (31.7 mg, 0.317 mmol, Tyger Scientific), respectively. The reaction mixture was stirred at room temperature for 1 h. The reaction was monitored by thin layer chromatography (silica gel, 15% methanol in ethyl acetate). The reaction mixture was concentrated to dryness, and the crude residue was purified by high performance liquid chromatography (C18-silica gel, eluting with a gradient of 5-95% acetonitrile in water) to give cis-4-[(4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one as white solid (98 mg, 86%). HR-MS (ES, m/z) calculated for C27H26N5O3Cl2[(M+H)+] 538.1407, observed 538.1408.

後処理

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe crude residue was purified by high performance liquid chromatography (C18-silica gel
  3. washeluting with a gradient of 5-95% acetonitrile in water)

出典と根拠

ORDレコード
ord-d98ba7de5b7e40c088260aae7017e05a
出典データセット
uspto-grants-2010_04
特許番号
US07705007B2

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