Sodium Carbonate Monohydrate → HCID 178476556, Verbindung

HRID 897616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897616
[O:1]1[CH2:5][CH:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10](B3[O:17][C:16]([CH3:19])(C)C(C)(C)O3)=[CH:9][CH:8]=2)[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.I[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2[NH2:36])[N:29]([C@H:37]2[CH2:42][CH2:41][C@H:40]([N:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)[CH2:39][CH2:38]2)[N:28]=1.[OH2:50].C(=O)([O-])[O-:52].[Na+].[Na+]>COCCOC.O>[C:16]([OH:52])(=[O:17])[CH3:19].[C:2]([OH:1])(=[O:50])[CH3:3].[O:1]1[CH2:5][CH:4]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:27]3[C:35]4[C:30](=[N:31][CH:32]=[N:33][C:34]=4[NH2:36])[N:29]([C@H:37]4[CH2:38][CH2:39][C@H:40]([N:43]5[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]5)[CH2:41][CH2:42]4)[N:28]=3)=[CH:11][CH:12]=2)[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2

Komponenten

6

Edukt 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22346766N-(2,3-dihydrobenzo[b]furan-3-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amineHCID 178481015HCID 178481015, Verbindung

Produkt 1

HCID 178476556HCID 178476556, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of N-(2,3-dihydrobenzo[b]furan-3-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.089 g, 0.000265 mol), trans-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.090 g, 0.000204 mol), tetrakis-(triphenylphosphine)palladium (0.014 g, 0.000012 mol) and sodium carbonate monohydrate (0.063 g, 0.00051 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 trans-3-[4-(2,3-dihydrobenzo[b]furan-3-ylamino)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.078 g, 0.000121 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-b1f8b398eeb74b19a02717b918b82b73
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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