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 2105036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105036
[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]

Komponenten

5

Edukt 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

Produkt 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)benzenamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-240d32b940be48dfb4ec44ed50fa5ade
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

Notizen zur Reaktion

Wird geladen…