Triethylamine → HCID 17859427, compound

HRID 1372697Notes

Reaction equation

HRID 1372697 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([OH:19])=O)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:26][C:27]1[CH:28]=[C:29]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:30]=[CH:31][C:32]=1[NH2:33].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH:33][C:32]2[CH:31]=[CH:30][C:29]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:28][C:27]=2[Cl:26])=[O:19])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 336711-benzyl-1H-indole-3-carboxylic acidHCID 65578Oxalyl chlorideHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 17859427HCID 17859427, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of 1-benzylindole-3-carboxylic acid (201.3 mg, 0.801 mmol) in methylene chloride (4.0 ml) was added oxalyl chloride (103.1 μl, 1.202 mmol) under stirring at −15° C. The reaction mixture was stirred at room temperature for 2.5 hours and then, distilled under reduced pressure to remove the solvent. The residue was dissolved in methylene chloride (4.0 ml) and to the resulting solution were added a solution of methyl 3-chloro-4-aminophenylacetate (167.9 mg, 0.841 mmol) in methylene chloride (4.0 ml) and triethylamine (0.35 ml, 2.523 mmol) under stirring at room temperature. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with chloroform, washed with 1N HCl, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate (341.3 mg, 98%) was obtained. The compound was provided for the subsequent reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in methylene chloride (4.0 ml) and to the resulting solution
  5. stirringunder stirring at room temperature
  6. stirringThe reaction mixture was stirred at room temperature for 18 hours
  7. distillationThe reaction mixture was distilled under reduced pressure
  8. customto remove the solvent
  9. additionThe residue was diluted with chloroform
  10. washwashed with 1N HCl
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationdistilled under reduced pressure
  13. customto remove the solvent

Sources & evidence

ORD record
ord-bd34bfa642f741d8a72bc6028498ce32
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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