Sodium Carbonate → HCID 59023001, Verbindung

HRID 1366201

Reaktionsgleichung

Reaktionsgleichung von HRID 1366201
[N:1]1(C2C=CC(NC3C4N(C=CN=4)C(C4C=C5C(=CC=4)C(=O)NC5)=CN=3)=CC=2)CCOCC1.Br[C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:55][CH2:54][N:53]([CH:56]([CH3:58])[CH3:57])[CH2:52][CH2:51]3)=[CH:46][CH:45]=2)=[N:36][CH:35]=1.CC1(C)C(C)(C)OB([C:67]2[CH:68]=[C:69]([C:72]([NH2:74])=[O:73])[O:70][CH:71]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[NH3:1].[CH:56]([N:53]1[CH2:54][CH2:55][N:50]([C:47]2[CH:48]=[CH:49][C:44]([NH:43][C:37]3[C:38]4[N:39]([CH:40]=[CH:41][N:42]=4)[C:34]([C:67]4[CH:68]=[C:69]([C:72]([NH2:74])=[O:73])[O:70][CH:71]=4)=[CH:35][N:36]=3)=[CH:45][CH:46]=2)[CH2:51][CH2:52]1)([CH3:58])[CH3:57]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 573939935-[8-(4-Morpholin-4-yl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-2,3-dihydro-isoindol-1-oneHCID 575899904-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxamideHCID 59022995(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine

Produkt 2

HCID 222AmmoniaHCID 59023001HCID 59023001, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In the same way as described for Compound 178, step 4, using, 5-bromo-imidazo[1,2-a]pyrazin-8-yl-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine (0.08 g, 0.19 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylic acid amide (0.092 g, 0.39 mmol), 1.5M Na2CO3 (1.02 mL, 1.53 mmol) and Pd(PPh3)4 (0.055 g, 0.47 mmol) in dioxane (4 mL). Purification using silica gel column chromatography, eluting with DCM followed by 97:3 DCM:NH3 (7M in MeOH), affords the title compound (30.2 mg, 36%).

Aufarbeitung

  1. customPurification
  2. washeluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-0d4d16133e4c4e7a9be92c3b201407c3
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893058B2

Verknüpfte Notizen

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