Cesium carbonate → HCID 178477895, compound

HRID 1842510Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.Cl.Cl.[NH:17]1[CH2:20][CH:19]([C:21]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:23]=3[N:22]=2)[CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:30][C:28]1[CH:27]=[CH:26][C:24]2[NH:25][C:21]([CH:19]3[CH2:18][N:17]([C:2]4[CH:7]=[C:6]([O:8][CH:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)[CH:5]=[CH:4][N:3]=4)[CH2:20]3)=[N:22][C:23]=2[CH:29]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-chloro-4-(tetrahydro-2H-pyran-4-yloxy)pyridine (0.060 g, 0.27 mmol), 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride (as described in Preparation 5) (0.076 g, 0.27 mmol), and cesium carbonate (0.35 g, 1.09 mmol) in NMP (0.5 mL) was heated to 130° C. for 24 h, then cooled to RT. Ethyl acetate and saturated aqueous ammonium chloride were added and the resulting biphasic mixture was separated. The organic layer was washed with water (2×), brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 5-chloro-2-(1-(4-(tetrahydro-2H-pyran-4-yloxy)pyridin-2-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.024 g, 0.062 mmol, 23% yield) as a light yellow solid. [M+1] 385. IC50 (uM) 1.087.

Workup

temperaturecooled to RT
customthe resulting biphasic mixture was separated
washThe organic layer was washed with water (2×), brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give an oil that
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-53530e66c060452ab873029eaf2815c7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946230B2

Reaction notes

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