Potassium Carbonate → [3-[2-[1-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamino]ethoxy]phenyl]acetic acid methyl ester

HRID 420595Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([N:9]3[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:17][O:18][C:19](=[O:31])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29]Br)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:17][O:18][C:19](=[O:31])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][NH:14][CH:11]2[CH2:12][CH2:13][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=4[N:6]=3)[CH2:10]2)[CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-ylamine (190 mg), [3-(2-bromoethoxy)phenyl]acetic acid methyl ester (205 mg) and potassium carbonate (114 mg) was stirred at 80° C. for 2 hours. To the reaction solution, was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (174 mg). Yield: 52%.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulphate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record: ord-1013c5b79c77404f987c34223a26b60d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097610B2

Reaction notes

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