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1,4-Dioxane → 3-Methoxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol

HRID 1027225
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1027225
O1CCOCC1.C([Si]([O:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[C:17]([O:30][CH3:31])[CH:16]=1)(C)C)(C)(C)C.Cl[C:33]1[N:38]=[N:37][C:36]([N:39]([CH3:50])[CH:40]2[CH2:45][C:44]([CH3:47])([CH3:46])[NH:43][C:42]([CH3:49])([CH3:48])[CH2:41]2)=[CH:35][CH:34]=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:31][O:30][C:17]1[CH:16]=[C:15]([OH:14])[CH:20]=[CH:19][C:18]=1[C:33]1[N:38]=[N:37][C:36]([N:39]([CH3:50])[CH:40]2[CH2:45][C:44]([CH3:46])([CH3:47])[NH:43][C:42]([CH3:49])([CH3:48])[CH2:41]2)=[CH:35][CH:34]=1
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Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 867105396-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine2×HCID 86710628Tert-butyl(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane

Produkt 1

HCID 1363771523-Methoxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol
Ausbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
72 °C

Versuchsvorschrift

A 20 L jacketed reactor fitted with a reflux condenser, N2 inlet, thermocouple and overhead stirrer was charged with 2.7 L of dioxane followed by tert-butyl(3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane (290 g, 557 mmol), 6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (Intermediate 1-1, 113 g, 398 mmol), and sodium bicarbonate (100 g, 1194 mmol). 700 mL of water was added, followed by addition of Pd(PPh3)4 (27.6 g, 23.88 mmol). The reaction mixture was heated at 72° C. overnight. After cooling to RT, the layers were separated. The organic layer was concentrated, and the reside was purified by silica gel chromatography using 5% MeOH (containing 1% TEA) in DCM to provide the desired product, 3-methoxy-4-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)phenol (83 g, 211 mmol, 53% yield). MS=371.4.

Aufarbeitung

  1. customfitted with a reflux condenser, N2 inlet
  2. temperatureAfter cooling to RT
  3. customthe layers were separated
  4. concentrationThe organic layer was concentrated
  5. customthe reside was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-959fae3c1a954c4ea14a48938bb53af9
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729263B2

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