Sodium Carbonate Monohydrate → HCID 178476517, Verbindung

HRID 432325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432325
[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13](B3[O:20][C:19]([CH3:22])(C)C(C)(C)O3)=[CH:12][CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:26]1[C:34]2[C:29](=[N:30][CH:31]=[N:32][C:33]=2[NH2:35])[N:28]([C@H:36]2[CH2:41][CH2:40][C@@H:39]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)[CH2:38][CH2:37]2)[N:27]=1.O.[C:50](=[O:53])([O-])[O-:51].[Na+].[Na+]>COCCOC.O>[C:19]([OH:51])(=[O:20])[CH3:22].[C:50]([OH:51])(=[O:53])[CH3:1].[CH3:48][N:45]1[CH2:46][CH2:47][N:42]([C@@H:39]2[CH2:38][CH2:37][C@H:36]([N:28]3[C:29]4=[N:30][CH:31]=[N:32][C:33]([NH2:35])=[C:34]4[C:26]([C:13]4[CH:12]=[CH:11][C:10]([NH:9][CH:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH3:8])=[CH:15][CH:14]=4)=[N:27]3)[CH2:41][CH2:40]2)[CH2:43][CH2:44]1

Komponenten

6

Edukt 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22346898α-Methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenemethanamineHCID 178481014HCID 178481014, Verbindung

Produkt 1

HCID 178476517HCID 178476517, VerbindungAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of N-(1-phenylethyl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.070 g, 0.000235 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.080 g, 0.000181 mol), tetrakis-(triphenylphosphine)palladium (0.012 g, 0.000011 mol) and sodium carbonate monohydrate (0.056 g, 0.00045 mol) was heated in a mixture of ethylene glycol dimethyl ether (5 mL) and water (3 mL) at 80° C. for sixteen hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield Cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-{4-[(1-phenylethyl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.062 g, 0.0000984 mol) as a white solid.

Aufarbeitung

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-bfc4f65525b6409299dead8e4eb0fbce
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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