Potassium Carbonate → HCID 68428607, compound

HRID 642319Notes

Reaction equation

HRID 642319 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[CH2:20]([O:22][C:23](=[O:37])[CH2:24][NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[O:35][CH3:36])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=2)=[N:8][C:7]=1[CH2:18][N:25]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[O:35][CH3:36])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:37])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68428197HCID 68428197, compound

Product 1

HCID 68428607HCID 68428607, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromomethyl-2-(5-bromo-pyridin-3-yl)-thiazole-5-carboxylic acid ethyl ester (880 mg, 2.18 mmol), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (552 mg, 2.18 mmol) and potassium carbonate (452 mg, 3.27 mmol) in anhydrous dimethylformamide (8 mL) was stirred at room temperature for 24 h before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil (495 mg): MS: (+) m/z 600.40, 602.20 (M+Na+, 79Br/81Br).

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-934ebcfa0e4f4d628358d6af80923111
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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