Sodium Carbonate → Ammonia

HRID 1924985

Reaktionsgleichung

Reaktionsgleichung von HRID 1924985
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][NH:35][CH:36]=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>[NH3:4].[O:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:5]3[C:6]4[N:7]([CH:8]=[CH:9][N:10]=4)[C:2]([C:32]4[CH:33]=[N:34][NH:35][CH:36]=4)=[CH:3][N:4]=3)=[N:13][CH:14]=2)[CH2:19][CH2:20]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59023091(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine

Produkt 2

HCID 222AmmoniaHCID 59023111N-(5-Morpholinopyridin-2-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In the same way as described for compound 127, step 4 using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine (100 mg, 0.266 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (77.6 mg, 0.4 mmol), Pd(PPh3)4 (77 mg, 0.066 mmol) and 1.5M Na2CO3 (1.42 mL, 2.13 mmol) in dioxane (4 mL). The crude compound is purified by silica gel column chromatography eluting with 96:4 DCM:NH3 (7M in MeOH) to afford the title compound which is triturated with diethyl ether (12.9 mg, 8%) and converted into the mesylate salt (6.1 mg, 38%)

Aufarbeitung

  1. customThe crude compound is purified by silica gel column chromatography
  2. washeluting with 96:4 DCM

Quellen und Nachweise

ORD-Eintrag
ord-18af632830ff4f519e836297a69a350e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178530B2

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