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1,2-Dichloroethane → Tert-butyl 2-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]carbonyl}hydrazinecarboxylate

HRID 490884
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 490884
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([OH:21])=O)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[NH:37][NH2:38]>CN(C=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([NH:38][NH:37][C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:21])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 534878291-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Produkt 1

HCID 57675152Tert-butyl 2-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]carbonyl}hydrazinecarboxylate
Ausbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of Intermediate 17 (1.48 g), EDC (1.34 g) and HOBT (0.83 g) in DMF (20 ml) was stirred at room temperature for 30 min. t-Butyl carbazate (0.68 g) was then added and stirring continued under nitrogen for a further 66 h. The mixture was concentrated in vacuo and the residue divided into two portions for purification. Each portion was applied to an SPE cartridge (aminopropyl, 10 g) which was eluted with methanol and the combined eluents were concentrated in vacuo. Further purification was carried out by Biotage (silica, 40 g), eluting with cyclohexane:ethyl acetate (1:4). Fractions containing desired material were combined and concentrated in vacuo to afford Intermediate 18 (1.39 g). LCMS showed MH+=405; Tm=2.64 min.

Aufarbeitung

  1. additionwas then added
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue divided into two portions for purification
  4. washwas eluted with methanol
  5. concentrationthe combined eluents were concentrated in vacuo
  6. customFurther purification
  7. washeluting with cyclohexane:ethyl acetate (1:4)
  8. additionFractions containing desired material
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5aeeff560ead445a94d25c3cb2aef2c5
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07528148B2

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