Ethylene Glycol → HCID 59421794, compound

HRID 499918Notes

Reaction equation

HRID 499918 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:28]([OH:30])=[O:29])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH:16]=2)=[O:10])=[C:4]([CH3:31])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:44](O)[CH2:45][OH:46].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:28]([O:30][CH2:44][CH2:45][OH:46])=[O:29])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH:16]=2)=[O:10])=[C:4]([CH3:31])[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59421809HCID 59421809, compound

Product 1

HCID 59421794HCID 59421794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.36 g (3 mmol) of 4-({[(4-chloro-2-methylphenyl)amino]carbonyl}amino)-1-[4-(trifluoromethyl)benzyl]-1H-imidazole-2-carboxylic acid (Example 20A) are dissolved in 6 ml of absolute DMF, and 0.58 g (3.6 mmol) of N,N-carbonyldiimidazole is added. The reaction mixture is stirred at RT for 3 h. Then 18.4 g (16.5 ml, 297 mmol) of 1,2-ethanediol and 303 mg (418 μl, 3 mmol) of triethylamine are added. The reaction mixture is stirred at 50° C. for 1.5 h and at RT overnight. Dilution with water is followed by extraction twice with ethyl acetate. The combined extracts are washed twice with saturated sodium bicarbonate solution, once with water and twice with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue from evaporation is purified by chromatography on silica gel with cyclohexane/ethyl acetate as eluent.

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 1.5 h and at RT overnight
  2. extractionDilution with water is followed by extraction twice with ethyl acetate
  3. washThe combined extracts are washed twice with saturated sodium bicarbonate solution, once with water and twice with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue from evaporation
  7. customis purified by chromatography on silica gel with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-2609e2b3d180459da51e31a25593a137
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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