Cesium carbonate → HCID 59374079, compound

HRID 473700Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[C:9]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]2)=[N:10][CH:11]=[CH:12][N:13]=1.[F:23][C:24]1[CH:29]=[C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:27]=[CH:26][C:25]=1[OH:37]>CN1C(=O)CCC1>[F:23][C:24]1[CH:29]=[C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:27]=[CH:26][C:25]=1[O:37][C:8]1[C:9]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]2)=[N:10][CH:11]=[CH:12][N:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of cesium carbonate (1.11 g, 3.41 mmol), 1-(4-(3-chloropyrazin-2-yl)piperidin-1-yl)ethanone (0.336 g, 1.40 mmol), and 2-fluoro-4-(pyridin-2-ylamino)phenol (0.547 g, 2.68 mmol) was added NMP (3 mL). The reaction mixture was degassed and heated to 120° C. for 1.5 h. The reaction mixture was diluted with EtOAc and the organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (40% to 100% EtOAc in hexanes) gave 1-(4-(3-(2-fluoro-4-(pyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone as a white solid. MS (ESI, pos. ion) m/z: 408.2 (M+1). IC50 (uM) 0.008056.

Workup

customThe reaction mixture was degassed
additionThe reaction mixture was diluted with EtOAc
washthe organic phase was washed with water (2×), brine (1×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by flash column chromatography on silica gel (40% to 100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-59a023298dc74e0c98cf55370b290e84
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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