Potassium Carbonate → HCID 58614653, compound

HRID 923163Notes

Reaction equation

HRID 923163 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+].[CH3:38][CH:39]1[O:44][CH:43]([CH3:45])[CH2:42][NH:41][CH2:40]1>CN(C=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:24]=[CH:25][C:26]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])=[C:5]([O:4][CH2:3][CH2:2][N:41]3[CH2:40][CH:39]([CH3:38])[O:44][CH:43]([CH3:45])[CH2:42]3)[CH:6]=2)=[CH:12][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1108622,6-DimethylmorpholineHCID 66877367HCID 66877367, compound

Product 1

HCID 58614653HCID 58614653, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 2,6-dimethylmorpholine (14 μl, 0.11 mmol), and stirred at room temperature for 18 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 20 mg of N-(4-chloro-3-(pyridin-2-yl)phenyl)-3-(2-(2,6-dimethylmorpholino)ethoxy)-4-(methylsulfonylmethyl)benzamide. MS (Q1) 571 (M)+.

Workup

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

Sources & evidence

ORD record
ord-404f68b4a64248fc8db818491e176678
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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