Cesium carbonate → HCID 86680465, compound

HRID 240456Notes

Reaction equation

[OH:1][CH:2]1[C:17](=[O:18])[N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][CH:4]2[CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1[CH:31]=[N:30][C:29]([CH:32]2[CH2:34][CH2:33]2)=[CH:28][N:27]=1>C(#N)C>[CH:32]1([C:29]2[N:30]=[CH:31][C:26]([O:1][CH:2]3[C:17](=[O:18])[N:5]4[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:9][CH:4]4[CH2:3]3)=[N:27][CH:28]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product from Example 207B (89 mg, 0.347 mmol) in anhydrous acetonitrile (3.5 mL) was added cesium carbonate (226 mg, 0.695 mmol) and 2-bromo-5-cyclopropylpyrazine (104 mg, 0.521 mmol). The resulting mixture was stirred under N2 at 50° C. for 48 hours. The mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate (3×). The combined organic layers were dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2 to give the title compound (82 mg, 63%).

Workup

temperatureto cool to room temperature
custompartitioned between water and ethyl acetate (3×)
dry with materialThe combined organic layers were dried over Na2SO4
customThe drying agent was removed by filtration
concentrationthe filtrate was concentrated in vacuo
customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2

Sources & evidence

ORD record: ord-682614dd95f94014bde68f6f8b336487
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648074B2

Reaction notes

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