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Triethylamine → Ethyl(E)-3-[6-[(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazin-8-yl)-(tert-butyldimethylsiloxy)methyl]pyridin-2-yl]-2-propenoate

HRID 1059409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1059409
Br[C:2]1[N:7]=[C:6]([CH:8]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:9]2[CH:10]=[CH:11][C:12]3[S:17][C:16]4[N:18]=[CH:19][CH:20]=[N:21][C:15]=4[N:14]([CH2:22][O:23][CH3:24])[C:13]=3[CH:25]=2)[CH:5]=[CH:4][CH:3]=1.[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH3:24][O:23][CH2:22][N:14]1[C:13]2[CH:25]=[C:9]([CH:8]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:6]3[N:7]=[C:2](/[CH:36]=[CH:35]/[C:34]([O:38][CH2:39][CH3:40])=[O:37])[CH:3]=[CH:4][CH:5]=3)[CH:10]=[CH:11][C:12]=2[S:17][C:16]2[N:18]=[CH:19][CH:20]=[N:21][C:15]1=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 186705248-[(6-Bromopyridin-2-yl)-(tert-butyldimethylsiloxy)methyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Produkt 1

HCID 18670598Ethyl(E)-3-[6-[(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazin-8-yl)-(tert-butyldimethylsiloxy)methyl]pyridin-2-yl]-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 0.72 g of 8-[(6-bromopyridin-2-yl)-(tert-butyldimethylsiloxy)methyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (8 ml) were added 0.17 ml of ethyl acrylate, 0.22 ml of triethylamine, 12 mg of palladium (II) acetate and 33 mg of triphenylphosphine and the resulting mixture was heated to 90° C. for 30 hours. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The organic layer was extracted, washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (diluted with dichloromethane/ethyl acetate) to thereby give 540 mg of the title compound as a yellow oily substance.

Aufarbeitung

  1. customwas brought back to room temperature
  2. extractionThe organic layer was extracted
  3. washwashed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (diluted with dichloromethane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1923915fbb0d43578a85e02b2137e2be
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518423B1

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