Methyl iodide → N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

HRID 2105036노트

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HRID 2105036 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[N:7]=[C:8]([CH:30]([C:44]3[CH:49]=[C:48]([O:50][CH2:51][CH3:52])[CH:47]=[C:46]([O:53][CH:54]([CH3:56])[CH3:55])[C:45]=3[F:57])[NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]4[N:42]=[C:41]([CH3:43])[O:40][N:39]=4)=[CH:34][CH:33]=3)[N:9]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=2)[CH:3]=[N:2]1.[H-].[Na+].[CH3:60]I>C1COCC1>[CH2:51]([O:50][C:48]1[CH:47]=[C:46]([O:53][CH:54]([CH3:56])[CH3:55])[C:45]([F:57])=[C:44]([CH:30]([C:8]2[N:9]([C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=[C:6]([C:4]3[CH:5]=[N:1][N:2]([CH3:60])[CH:3]=3)[N:7]=2)[NH:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([CH3:43])[O:40][N:39]=3)=[CH:34][CH:33]=2)[CH:49]=1)[CH3:52]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68815685N-((4-(1H-pyrazol-4-yl)-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

생성물 1

HCID 68814350N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of Intermediate 237.1 (30 mg, 0.04 mmol) in THF (1 mL) at 0° C. was added NaH (3.16 mg, 0.08 mmol), stirred at 0° C. for 30 min, then MeI was added and the reaction mixture was warmed up to rt over 1 h. The reaction mixture was then partitioned between EtOAc and sat. NH4Cl, the organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes, gradient) to afford 20 mg (62%) of Intermediate 237.2.

후처리

  1. temperaturethe reaction mixture was warmed up to rt over 1 h
  2. customThe reaction mixture was then partitioned between EtOAc and sat. NH4Cl
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes, gradient)

출처 및 근거

ORD 기록
ord-240d32b940be48dfb4ec44ed50fa5ade
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576098B2

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