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Triphenylphosphine → N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

HRID 2205730
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2205730
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]2[N:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N([Si](C)(C)C)=[N+]=[N-].N(C(OCC)=O)=NC(OCC)=O>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:18]3[N:17]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=4)[CH:15]=[CH:14][C:13]3=[N:12][N:11]=2)=[CH:4][CH:3]=1
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Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66849890N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide

Produkt 1

HCID 66849693N-(4-(3-(4-chlorobenzyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a round bottom flask was added N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide (0.928 mmole), triphenylphosphine (3.25 mmole), azidotrimethylsilane (3.25 mmole), diethyl azodicarboxylate (4.18 mmole), and THF (13 mL). The resulting mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with dichloromethane and washed with saturated NaHCO3 and brine. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was washed with dichloromethane and methanol. The yellow solid was further purified by recrystallization with DMF and water to yield N-(4-(3-(4-chlorobenzyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methanesulfonamide.

Aufarbeitung

  1. washwashed with saturated NaHCO3 and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated in vacuo
  5. washThe crude product was washed with dichloromethane and methanol
  6. customThe yellow solid was further purified by recrystallization with DMF and water

Quellen und Nachweise

ORD-Eintrag
ord-7f1045ae810f4a45a29243b7b42c0966
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09371329B2

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