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Piperidine → 3-(5-Methylisoxazol-3-yl)-6-(1-methyl-5-(piperidin-1-yl)methyl-1H-[1,2,3]triazol-4-ylmethoxy)-[1,2,4]triazolo[3,4-alpha]phthalazine

HRID 2183520
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Reaktionsgleichung

Reaktionsgleichung von HRID 2183520
S(Cl)(Cl)=O.[CH3:5][N:6]1[C:10]([CH2:11]O)=[C:9]([CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]3=[N:25][N:26]=[C:27]([C:28]4[CH:32]=[C:31]([CH3:33])[O:30][N:29]=4)[N:17]3[N:16]=2)[N:8]=[N:7]1.ClCC1N=NNC=1.[NH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>C(Cl)Cl>[CH3:33][C:31]1[O:30][N:29]=[C:28]([C:27]2[N:17]3[N:16]=[C:15]([O:14][CH2:13][C:9]4[N:8]=[N:7][N:6]([CH3:5])[C:10]=4[CH2:11][N:41]4[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]4)[C:24]4[C:19]([C:18]3=[N:25][N:26]=2)=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:32]=1
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Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 131724945[1-Methyl-4-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-alpha]phthalazine-6-yl]oxy}methyl)-1H-[1,2,3]triazol-5-yl]methanolHCID 178478443HCID 178478443, Verbindung

Produkt 1

HCID 102762793-(5-Methylisoxazol-3-yl)-6-(1-methyl-5-(piperidin-1-yl)methyl-1H-[1,2,3]triazol-4-ylmethoxy)-[1,2,4]triazolo[3,4-alpha]phthalazine
Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Thionyl chloride (625 μl, 8.6 mmol) was added to a stirred suspension of [1-methyl-4-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-α]phthalazine-6-yl]oxy}methyl)-1H-[1,2,3]triazol-5-yl]methanol (672 mg, 1.71 mmol) in CH2Cl2 (50 ml) and the mixture was stirred at room temperature for 1 h under N2, during which period the solid dissolved and then precipitated. The reaction mixture was concentrated under reduced pressure and then azeotroped with toluene (2×50 ml) and used without further purification. A portion of the crude chloromethyltriazole (125 mg, 0.30 mmol) and piperidine (0.30 ml, 3.0 mmol) in CH2Cl2 (6ml) were stirred at room temperature for 48 h under N2. The mixture was then concentrated under reduced pressure while dry loading onto silica and purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 solution as eluent to yield the desired phthalazine (126 mg, 90%), which was then recrystallised CH2Cl2/iso-hexanes. 1H NMR (360 MHz, CDCl3) δ 8.67 (1H, d, J=8.0 Hz), 8.14 (1H, d, J=8.0 Hz), 7.93 (1H, t, J=8.0 Hz), 7.75 (1H, d, J=8.0 Hz), 6.94 (1H, s), 5.77 (2H, s), 4.12 (3H, broad s), 3.70-3.60 (2H, m), 2.59 (3H, s), 2.40-2.30 (4H, m), 1.75-1.33 (6H, m).

Aufarbeitung

  1. dissolutiondissolved
  2. customprecipitated
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customazeotroped with toluene (2×50 ml)
  5. customused without further purification
  6. concentrationThe mixture was then concentrated under reduced pressure
  7. customwhile dry loading onto silica
  8. custompurified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 solution as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0c241ddb4abd4f8faf2cbec700e280d8
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06900209B2

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