Cesium carbonate → HCID 178477892, compound

HRID 1842512Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl.[NH:9]1[CH2:12][CH:11]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=3[N:14]=2)[CH2:10]1.Cl[C:24]1[CH:29]=[C:28]([CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:27]=[CH:26][N:25]=1>CC(N(C)C)=O>[Cl:22][C:20]1[CH:19]=[CH:18][C:16]2[NH:17][C:13]([CH:11]3[CH2:12][N:9]([C:24]4[CH:29]=[C:28]([CH:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)[N:27]=[CH:26][N:25]=4)[CH2:10]3)=[N:14][C:15]=2[CH:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of cesium carbonate (0.83 g, 2.56 mmol), 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride (as described in Preparation 5) (0.18 gg, 0.64 mmol), and 4-chloro-6-(tetrahydro-2H-pyran-4-yl)pyrimidine (0.13 g, 0.64 mmol) in DMA (1 mL) was heated to 70° C. for 18 h, then cooled to RT. The resulting suspension was partitioned between ethyl acetate and water, the layers were separated, and the organic layer was washed with water twice, brine once, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 5-chloro-2-(1-(6-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.11 g, 0.30 mmol, 47% yield) as a white solid. [M+1] 370. IC50 (uM) 1.283.

Workup

temperaturecooled to RT
customThe resulting suspension was partitioned between ethyl acetate and water
customthe layers were separated
washthe organic layer was washed with water twice
dry with materialbrine once, dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record: ord-1cde011bf36347c984808f53ced9ed8f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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