Water → HCID 67128878, Verbindung

HRID 2354092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354092
Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.Cl.Cl.[C:17]12([CH2:24][N:25]3[CH2:29][CH2:28][C@@H:27]([NH2:30])[CH2:26]3)[O:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.CCN(CC)CC.O>CC(N(C)C)=O>[C:17]12([CH2:24][N:25]3[CH2:29][CH2:28][C@@H:27]([NH:30][C:2]4[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=4)[CH2:26]3)[O:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 67128668HCID 67128668, VerbindungHCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

Produkt 1

HCID 67128878HCID 67128878, VerbindungAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of ethyl (2E)-3-(5-chloropyrazin-2-yl)acrylate (242.8 mg) in DMA (1.9 mL) was added (3R)-1-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)pyrrolidin-3-amine dihydrochloride (370 mg) and Et3N (796 uL), which was stirred at 100° C. for 24 hours. To the resultant was added H2O, which was extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (425 mg) as a brown solid.

Aufarbeitung

  1. extractionwas extracted with AcOEt
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d2428a02ba05420ba912df114e0a5722
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750155B2

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