Potassium Carbonate → 5-(1,4-Diazepan-1-yl)-2-pyridinyl phenyl sulfone methanesulfonic acid salt

HRID 23875

Reaction equation

[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](Cl)=[CH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-:18].[K+].[K+].[NH:23]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C>[CH3:10][S:7]([OH:8])(=[O:9])=[O:18].[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N:23]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of 5-chloro-2-pyridinyl phenyl sulfone (2.0 g, 7.9 mmol) in DMF (50 mL) was added potassium carbonate (2.5 g, 18 mmol) and homopiperazine (1.7 g, 17 mmol). The mixture was heated at 85° C. for 72 h. The mixture then was removed from heat and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water (2×100 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. Column chromatography (silica gel, 75 mL) using 5% CH3OH in CH2Cl2 with 0.7% NH4OH and conversion to the methanesulfonate salt gave 0.182 g of the title compound; IR (drift) 1570, 1304, 1240, 1223, 1207, 1196, 1178, 1145, 1112, 1059, 1052, 785, 715, 688, 645 cm−1. 1H NMR (DMSO-d6) δ2.0, 3.1, 3.2, 3.38, 3.56, 3.78, 7.26, 7.64, 7.88, 8.21, 8.67.

Workup

customThe mixture then was removed
temperaturefrom heat
custompartitioned between water and ethyl acetate
customThe layers were separated
washthe organic layer washed twice with water (2×100 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-57c79025038d40cb8650cc9c2598fcb7
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855709B2

Linked notes

Loading…