Sodium Carbonate → {3-[2-(4-Benzenesulfonylpiperazin-1-yl)ethoxy]phenyl}-(2-methylquinolin-4-yl)amine

HRID 914972

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([CH3:22])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:29]1([S:35]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[C:29]1([S:35]([N:38]2[CH2:43][CH2:42][N:41]([CH2:2][CH2:3][O:4][C:5]3[CH:6]=[C:7]([NH:11][C:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]=[C:14]([CH3:22])[CH:13]=4)[CH:8]=[CH:9][CH:10]=3)[CH2:40][CH2:39]2)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 21 (250 mg, 0.67 mmol) in DMF (5 mL) were sequentially added sodium carbonate (149 mg, 1.41 mmol). and 22 (183 mg, 0.808 mmol). The reaction was placed under a N2 atmosphere and heated at 90° C. for 16 hours. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and washed with water and brine. The ethyl acetate extracts were dried over anhydrous magnesium sulfate and evaporated. The residue was purified via reversed phase HPLC to yield the title compound as a pale yellow solid (20 mg, 6%).

Workup

temperatureAfter cooling to room temperature
extractionthe reaction mixture was extracted with ethyl acetate
washwashed with water and brine
dry with materialThe ethyl acetate extracts were dried over anhydrous magnesium sulfate
customevaporated
customThe residue was purified via reversed phase HPLC

Sources & evidence

ORD record: ord-c6be2016b6194acba03768c126480de2
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265122B2

Linked notes

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