Cesium carbonate → HCID 68685955, compound

HRID 2238634Notes

Reaction equation

HRID 2238634 reaction equation
Br[C:2]1[C:3]([C:20]2[N:24]3[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]3=[N:22][CH:21]=2)=[N:4][C:5]([N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:78][N:79]1[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1.C(=O)([O-])O.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.O1CCOCC1.C1(C)C=CC=CC=1>[CH3:29][C:28]1[C:23]2[N:24]([C:20]([C:3]3[C:2]([N:82]4[CH2:83][CH2:84][N:79]([CH3:78])[CH2:80][CH2:81]4)=[CH:7][N:6]=[C:5]([N:8]([C@H:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH3:13])[C:9](=[O:11])[CH3:10])[N:4]=3)=[CH:21][N:22]=2)[CH:25]=[CH:26][CH:27]=1

Participants

10

Reactant 5

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68690037HCID 68690037, compound

Product 1

HCID 68685955HCID 68685955, compound

Reagents, catalysts & solvents 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 17 mg of N-[5-bromo-4-(8-methylimidazo[1,2-a]pyridin-3-yl)-2-pyrimidinyl]-N-[(1S)-1-phenylethyl]acetamide [16-1], 2.17 mg of bis(dibenzylideneacetone)palladium, 19 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 17.2 mg of cesium carbonate, 5.0 μL of 1-methylpiperazine, 0.25 mL of toluene, and 0.5 mL of 1,4-dioxane, was stirred at 80° C. for 3 days. After cooling the reaction mixture back to room temperature, a saturated aqueous solution of sodium hydrogen carbonate and water were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by preparative reversed phase liquid chromatography, to obtain 0.6 mg of N-[4-(8-methylimidazo[1,2-a]pyridin-3-yl)-5-(4-methyl-1-piperazinyl)-2-pyrimidinyl]-N-[(1S)-1-phenylethyl]acetamide [16-2].

Workup

  1. temperatureAfter cooling the reaction mixture back to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by preparative reversed phase liquid chromatography

Sources & evidence

ORD record
ord-1ce4819ae3b94a398cf930dbafe03e82
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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