5,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one → 5,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 4167

Reaktionsgleichung

Reaktionsgleichung von HRID 4167
C([Li])CCC.[N:6]1[C:11]2[NH:12][C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15](=[O:17])[NH:16][C:10]=2[CH:9]=[CH:8][CH:7]=1.[C:22](Cl)(=[O:27])[CH2:23][CH2:24][C:25]#[CH:26]>CCCCCC.O1CCCC1.C(OCC)(=O)C>[O:27]=[C:22]([N:12]1[C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15](=[O:17])[NH:16][C:10]2[CH:9]=[CH:8][CH:7]=[N:6][C:11]1=2)[CH2:23][CH2:24][C:25]#[CH:26]

Komponenten

7

Edukt 3

HCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 13128357Pent-4-ynoyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 137291885,11-dihydro-11-[1-oxo-4-pentynyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

22.4 ml of a 1.6 molar solution of n-butyl-lithium in n-hexane are added dropwise with stirring, at 0° C., to a suspension of 3.7 g (0.017 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 150 ml of absolute tetrahydrofuran. After it has all been added, the mixture is stirred for a further 30 minutes and then mixed with a solution of 2.04 g (0.0175 mol) of 4-pentynoic acid chloride in 20 ml of tetrahydrofuran. The mixture is heated to 30° C. and stirred for a further hour. The reaction mixture is then poured into a saturated saline solution. The organic phase is diluted with ethyl acetate and, after being separated off, washed twice with saline solution, filtered over charcoal and evaporated to dryness in vacuo. The crude product is purified by column chromatography on silica gel using chloroform as eluant. 2.2 g (43% of theory) of colourless crystals were obtained, melting point 179°-180° C.

Aufarbeitung

  1. additionall been added
  2. stirringstirred for a further hour
  3. additionThe reaction mixture is then poured into a saturated saline solution
  4. customafter being separated off
  5. washwashed twice with saline solution
  6. filtrationfiltered over charcoal
  7. customevaporated to dryness in vacuo
  8. customThe crude product is purified by column chromatography on silica gel
  9. custom2.2 g (43% of theory) of colourless crystals were obtained

Quellen und Nachweise

ORD-Eintrag
ord-74fbee929e784564bd98215859d583b0
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724236

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