Cesium carbonate → HCID 56655449, compound

HRID 1431042Notes

Reaction equation

HRID 1431042 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.C([O:24][CH2:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][C:27]=1[N:41]1[N:50]=[CH:49][C:48]2[C:43](=[C:44]([F:55])[CH:45]=[C:46]([C:51]([CH3:54])([CH3:53])[CH3:52])[CH:47]=2)[C:42]1=[O:56])(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C.CCCCCC>[C:51]([C:46]1[CH:47]=[C:48]2[C:43](=[C:44]([F:55])[CH:45]=1)[C:42](=[O:56])[N:41]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([C:2]3[CH:3]=[C:4]([NH:10][C:11]4[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][N:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=3)[C:26]=1[CH2:25][OH:24])[N:50]=[CH:49]2)([CH3:54])([CH3:52])[CH3:53]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 594737692-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetateHCID 667425346-Chloro-4-(5-methanesulfonyl-pyridin-2-ylamino)-2-methyl-2H-pyridazin-3-one

Product 1

HCID 56655449HCID 56655449, compound

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
130 °C

Procedure

6-Chloro-4-(5-methanesulfonyl-pyridin-2-ylamino)-2-methyl-2H-pyridazin-3-one (40 mg, 127 μmol, Eq: 1.00), 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (136 mg, 165 μmol, Eq: 1.3) and cesium carbonate (145 mg, 445 μmol, Eq: 3.5) were dissolved in 10% aq. dioxane solution (3.3 ml). The reaction mixture was heated to 130° C. for 30 min in the microwave. Reaction mixture was filtered over celite. Filtrate was extracted with ethyl acetate, washed with water, and then with brine. Organic phase was dried over sodium sulfate; filtered; concentrated to give light brown solid. The crude material was dissolved in ethyl acetate, and treated with hexane until a precipitate was formed. Precipitate was collected by filtration to give an off-white solid. Solid was dissolved in dioxane (2 ml) and 1 M sodium hydroxide solution (191 μl, 191 μmol, Eq: 1.5) was added and stirred at room temperature overnight+

Workup

  1. customReaction mixture
  2. filtrationwas filtered over celite
  3. extractionFiltrate was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialOrganic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give light brown solid
  9. customwas formed
  10. filtrationPrecipitate was collected by filtration
  11. customto give an off-white solid

Sources & evidence

ORD record
ord-2b3901377f854884a055ecd15fd03565
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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