Cesium carbonate → HCID 59374076, compound

HRID 473698Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.F[C:16]1[C:17]([CH:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]2)=[N:18][CH:19]=[CH:20][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[C:17]([CH:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH2:27]3)=[N:18][CH:19]=[CH:20][N:21]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-(pyridin-2-ylamino)phenol (47 mg, 0.25 mmol), 1-(4-(3-fluoropyrazin-2-yl)piperidin-1-yl)ethanone (56 mg, 0.25 mmol), and cesium carbonate (123 mg, 0.376 mmol) in DMSO (0.85 mL) was heated at 80° C. for 20 h. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was back extracted with EtOAc (2×) and the combined organic layer was dried (Na2SO4) and concentrated. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 100% EtOAc in hexane, then 3% MeOH in EtOAc, to provide 1-(4-(3-(4-(pyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone as off-white solid. MS (ESI, pos. ion) m/z: 389.9 (M+1). IC50 (uM) 0.003589.

Workup

customThe reaction mixture was partitioned between EtOAc and brine
extractionThe aqueous layer was back extracted with EtOAc (2×)
dry with materialthe combined organic layer was dried (Na2SO4)
concentrationconcentrated
customThe crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
washeluting with a gradient of 0% to 100% EtOAc in hexane

Sources & evidence

ORD record: ord-4de8a5cb99e04e9cb2fbf1e727761160
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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