Ethanolamine → HCID 59421793, compound

HRID 499917Notes

Reaction equation

HRID 499917 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)[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.[NH2:44][CH2:45][CH2:46][OH:47].[Cl-].[Na+]>CN(C=O)C.O>[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]([NH:44][CH2:45][CH2:46][OH:47])=[O:30])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:20][CH:19]=3)[CH:16]=2)=[O:10])=[C:4]([CH3:31])[CH:3]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 5234Sodium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 59421809HCID 59421809, compound

Product 1

HCID 59421793HCID 59421793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.81 g (4 mmol) of 4-({[(4-chloro-2-methylphenyl)amino]carbonyl}amino)-1-[4-(trifluoromethyl)benzyl]-1H-imidazole-2-carboxylic acid (Example 20A) are dissolved in 16 ml of absolute DMF, and 1.94 g (12 mmol) of N,N-carbonyldiimidazole are added. The reaction mixture is stirred at RT for 1.5 h and, after addition of 144 μl of water, stirred at RT for 10 min. Then 366 mg (6 mmol) of 2-aminoethanol are added, and the mixture is stirred at RT for 1 h. The reaction mixture is mixed with saturated sodium chloride solution and extracted twice with ethyl acetate. The combined extracts are washed once each with 10% strength citric acid, saturated sodium bicarbonate solution, water and saturated sodium chloride solution, dried with magnesium sulphate and concentrated in vacuo. The residue from evaporation is purified by chromatography on silica gel with dichloromethane/methanol as eluent.

Workup

  1. stirringstirred at RT for 10 min
  2. stirringthe mixture is stirred at RT for 1 h
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts are washed once each with 10% strength citric acid, saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  5. dry with materialdried with magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue from evaporation
  8. customis purified by chromatography on silica gel with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-466d75e17bf147be90d2444800ef73a2
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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