Sodium hydride → (E)-tert-butyl 5-(2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)styryl)pyrazin-2-ylcarbamate

HRID 2199316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199316
C(OP([CH2:9][C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14][CH:15]=1)(OCC)=O)C.[H-].[Na+].[CH:26]([C:28]1[CH:29]=[C:30]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)=[C:39]([C:51]([F:54])([F:53])[F:52])[CH:38]=2)[CH:31]=[CH:32][C:33]=1[CH3:34])=O>CN(C=O)C>[CH3:34][C:33]1[CH:32]=[CH:31][C:30]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)=[C:39]([C:51]([F:53])([F:54])[F:52])[CH:38]=2)=[CH:29][C:28]=1/[CH:26]=[CH:9]/[C:10]1[N:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[N:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 59649414HCID 59649414, VerbindungHCID 86676738HCID 86676738, Verbindung

Produkt 1

HCID 68304566(E)-tert-butyl 5-(2-methyl-5-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamido)styryl)pyrazin-2-ylcarbamateAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

tert-butyl 5-((diethoxyphosphoryl)methyl)pyrazin-2-ylcarbamate (35 mg, 0.10 mmol) in dried DMF (0.5 mL) was added NaH (5 mg, 0.12 mmol) at 0° C. After 20 minutes, a solution N-(3-formyl-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (44 mg, 0.10 mmol) in dried DMF (0.5 mL) was added slowly into the reaction mixture. The reaction mixture was stirred overnight at room temperature and quenched by adding water. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (3% to 7% MeOH/CH2Cl2) as a solvent to afford title compound (40 mg, 64% yield). MS m/z: 611 [M+1].

Aufarbeitung

  1. customquenched
  2. additionby adding water
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4, celite
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8494a39618ef4984bdebd81290958d23
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09358231B2

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