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3,6-Dichloropyridazine → Tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

HRID 873566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873566
[NH:1]1[CH2:4][CH:3]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:2]1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[N:38]=[N:39][C:40](Cl)=[CH:41][CH:42]=1>C(O)C>[Cl:36][C:37]1[N:38]=[N:39][C:40]([N:1]2[CH2:4][CH:3]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([CH:14]4[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]4)=[CH:10][CH:9]=3)=[O:6])[CH2:2]2)=[CH:41][CH:42]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 673313,6-DichloropyridazineHCID 81531DiisopropylethylamineHCID 86702043HCID 86702043, Verbindung

Produkt 1

HCID 86702042Tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

In a 50 mL round-bottomed flask was added tert-butyl 4-(4-(azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate (918 mg, 2.55 mmol) and diisopropylethylamine (0.558 ml, 3.19 mmol) in ethanol (10.6 ml). 3,6-dichloropyridazine (317 mg, 2.128 mmol) was added as a solid in a single portion. The reaction was stirred overnight at 45° C.; and the reaction was cooled and concentrated. Dichloromethane and water were added and the layers were separated. The aqueous layer was extracted three times with dichloromethane and the combined organics were dried with magnesium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography to give the title compound.

Aufarbeitung

  1. temperatureand the reaction was cooled
  2. concentrationconcentrated
  3. additionDichloromethane and water were added
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted three times with dichloromethane
  6. dry with materialthe combined organics were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by regular phase flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ef4b77b9051e4133a176093c0841bda9
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975398B2

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