Potassium Acetate → 6-Methyl-4-[8-(4-morpholin-4-ylphenylamino)-imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-one

HRID 1921802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921802
C(OC(=O)[N:7]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1)[C:8]1[C:9]2[N:10]([CH:23]=[CH:24][N:25]=2)[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:12][N:13]=1)(C)(C)C.Br[C:40]1[CH:45]=[C:44]([CH3:46])[N:43]=[C:42]([O:47][Si](C(C)(C)C)(C)C)[CH:41]=1.CC([O-])=O.[K+]>O1CCOCC1>[CH3:46][C:44]1[NH:43][C:42](=[O:47])[CH:41]=[C:40]([C:11]2[N:10]3[CH:23]=[CH:24][N:25]=[C:9]3[C:8]([NH:7][C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:30][CH:31]=3)=[N:13][CH:12]=2)[CH:45]=1

Komponenten

5

Edukt 3

HCID 517044Potassium AcetateHCID 58423078(4-Morpholin-4-ylphenyl)-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)imidazo[1,2-a]pyrazin-8-yl]carbamic acid tert-butyl esterHCID 590230434-Bromo-2-((tert-butyldimethylsilyl)oxy)-6-methylpyridine

Produkt 1

HCID 590230826-Methyl-4-[8-(4-morpholin-4-ylphenylamino)-imidazo[1,2-a]pyrazin-5-yl]-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Half of the solution prepared in Step 3 and 4-bromo-2-(tert-butyldimethylsilyloxy)-6-methylpyridine (30 mg, 0.10 mmol) are mixed and diluted with dioxane (0.15 mL). KOAc (15 mg, 0.15 mmol) and Pd(dppf)Cl2DCM (2 mg, 0.0025 mmol) are added and the system is flushed with N2 and heated at 80° C. for 2.5 h. The mixture is cooled to rt, diluted with DCM (5 mL) and MeOH (1 mL) and filtered through celite. The solvents are evaporated, the residue is suspended in DCM (2 mL) and TFA (0.5 mL) is added, causing the solid to dissolve. The solution is stirred at rt overnight and the solvents are then evaporated. The residue is purified by preparative HPLC to afford the title compound as a yellow solid. LCMS: Rt=0.84 min (100%), m/z (ESI) 403 (M+H)+.

Aufarbeitung

  1. customthe system is flushed with N2
  2. temperatureThe mixture is cooled to rt
  3. additiondiluted with DCM (5 mL) and MeOH (1 mL)
  4. filtrationfiltered through celite
  5. customThe solvents are evaporated
  6. additionTFA (0.5 mL) is added
  7. dissolutionto dissolve
  8. customthe solvents are then evaporated
  9. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-da005fea253f4240bfb49d57bc73c34a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173656B2

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