Sodium hydride → HCID 66740166、化合物

HRID 1627318ノート

反応式

HRID 1627318 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Cl[CH2:18][C:19]1[N:20]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:21]([C:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)([CH3:26])[CH3:25])=[CH:22][N:23]=1>C1COCC1>[Cl:34][C:29]1[CH:28]=[C:27]([C:24]([C:21]2[N:20]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[C:19]([CH2:18][O:1][CH:2]3[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)=[N:23][CH:22]=2)([CH3:26])[CH3:25])[CH:32]=[CH:31][C:30]=1[Cl:33]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 667400042-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

生成物 1

HCID 66740166HCID 66740166、化合物収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (202 mg, 1 mmol) in anhyd THF (3 mL) was added NaH (60% in mineral oil, 53 mg, 1.32 mmol). The mixture stirred at room temperature for 30 min, then a solution of 2-(chloromethyl)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (262 mg, 0.66 mmol) in THF (2 mL) was added. After stirring at ambient temperature overnight, the reaction was quenched by addition of MeOH and concentrated in vacuo. The residue was partitioned in water and EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (silica, 0-90% EtOAc/Hex) to give tert-butyl 4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)methoxy)piperidine-1-carboxylate as a white solid (215 mg, 60%).

後処理

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe reaction was quenched by addition of MeOH
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned in water
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (silica, 0-90% EtOAc/Hex)

出典と根拠

ORDレコード
ord-7348cfd03871494d8cb805fda35816d3
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

読み込み中…