Sodium hydride → HCID 66740166, 화합물

HRID 1627318노트

반응식

HRID 1627318 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 66740166HCID 66740166, 화합물수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7348cfd03871494d8cb805fda35816d3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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