Potassium Carbonate → HCID 71294296, compound

HRID 240718Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:27]([NH:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[O:28])[CH:18]=[N:19][C:20]=2[O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:11][CH:10]=1.[C:36]([O:39][CH2:40][CH2:41]Br)(=[O:38])[CH3:37].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:27]([NH:29][N:30]3[CH2:31][CH2:32][N:33]([CH2:41][CH2:40][O:39][C:36](=[O:38])[CH3:37])[CH2:34][CH2:35]3)=[O:28])[CH:18]=[N:19][C:20]=2[O:21][CH2:22][C:23]([F:24])([F:26])[F:25])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-(4-Chloro-phenyl)-N-piperazin-1-yl-6-(2,2,2-trifluoro-ethoxy)-3-pyridinecarboxamide trifluoroacetate (1:1) (200 mg, 378 μmol, example 13b) was combined with acetonitrile (10 mL) to give a yellow solution. To this solution 2-bromoethyl acetate (760 mg, 500 μl, 4.55 mmol) and K2CO3 (157 mg, 1.13 mmol) were added successively. The reaction mixture was heated to 60° C., stirred for 20 h, filtered through a Celite® pad after cooling to ambient temperature and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 20 g, 0% to 50% methanol in ethyl acetate) to give the title compound (107 mg, 57%) as white solid; LC-MS (UV peak area/ESI) 97.8%, 501.1510 (M+H)+.

Workup

customto give a yellow solution
filtrationfiltered through a Celite® pad
temperatureafter cooling to ambient temperature
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by flash chromatography (silica gel, 20 g, 0% to 50% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-57096bee3db04353bd8384ea3a749e22
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648099B2

Reaction notes

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