Potassium Carbonate → HCID 58614845, compound

HRID 923162Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][C:26]=1[CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:12]=1)=[O:9].C(=O)([O-])[O-].[K+].[K+].[N:38]1([C:44](=[O:46])[CH3:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C=O)C>[C:44]([N:38]1[CH2:43][CH2:42][N:41]([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:24]=[CH:25][C:26]=2[CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:12]=2)=[O:9])[CH2:40][CH2:39]1)(=[O:46])[CH3:45]

Participants

Conditions

Temperature: 50 °C

Procedure

3-(2-Bromoethoxy)-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)benzamide (50 mg, 0.095 mmol) was dissolved in DMF (1.0 ml) and treated with potassium carbonate (18 mg, 0.13 mmol) and 1-(piperazin-1-yl)ethanone (15 mg, 0.11 mmol) for 18 hours. The reaction was heated for 2.0 hours at 50° C., then additional potassium carbonate (18 mg, 0.13 mmol) and 1-(piperazin-1-yl)ethanone (15 mg, 0.11 mmol) was added. After 2 hours, the reaction was quenched in 5% NaOH and extracted with ethyl acetate twice. The ethyl acetate extracts were washed with water once, brine once, dried with MgSO4, and purified by reverse phase HPLC to yield 18 mg of 3-(2-(4-acetylpiperazin-1-yl)ethoxy)-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)benzamide. MS (Q1) 543 (M)+.

Workup

customthe reaction was quenched in 5% NaOH
extractionextracted with ethyl acetate twice
washThe ethyl acetate extracts were washed with water once
dry with materialbrine once, dried with MgSO4
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-e1df96b88c5f47da814fc2d27d3da1fc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278961B2

Reaction notes

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