Acetic Acid → tert-butyl 4-(5-(2-acetylhydrazinecarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79561

Reaktionsgleichung

Reaktionsgleichung von HRID 79561
[CH2:1]([O:3]C1C=CC2C(=CC=CC=2)N1C(OCC)=O)[CH3:2].C(O)(=O)C.[NH:23]([C:25]([C:27]1[C:28]([N:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]2)=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1)=[O:26])[NH2:24]>C1COCC1.C(#N)C>[C:1]([NH:24][NH:23][C:25]([C:27]1[C:28]([N:36]2[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]2)=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1)=[O:26])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 68759320tert-Butyl 4-(5-(hydrazinecarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Produkt 1

HCID 68762103tert-butyl 4-(5-(2-acetylhydrazinecarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22177404Acetonitrile tetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 2-ethoxyquinoline-1(2H)-carboxylate (226 mg, 0.916 mmol) was added to acetic acid (50.0 mg, 0.832 mmol) in THF/ACN (5 mL), and the reaction was stirred at room temperature for 1 hour. tert-Butyl 4-(5-(hydrazinecarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (300 mg, 0.832 mmol) was added, and the reaction was heated to 70° C. for 1 hour. The solution was then concentrated to dryness. The resulting residue was crystallized from DCM to yield tert-butyl 4-(5-(2-acetylhydrazinecarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (241 mg, 71.9% yield) as a solid.

Aufarbeitung

  1. temperaturethe reaction was heated to 70° C. for 1 hour
  2. concentrationThe solution was then concentrated to dryness
  3. customThe resulting residue was crystallized from DCM

Quellen und Nachweise

ORD-Eintrag
ord-a83bcdd6e78d417f848d81596c5d6a57
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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