Triethylamine → HCID 17859043, compound

HRID 1372693Notes

Reaction equation

HRID 1372693 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[CH:5]1)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:26]=[CH:27][C:28]=1[NH2:29].C(N(CC)CC)C>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:26]=[CH:27][C:28]=1[NH:29][C:13]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 103979731-(1-Methylethyl)-1H-indole-3-carboxylic acidHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 17859043HCID 17859043, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution of 1-isopropylindole-3-carboxylic acid (159.6 mg, 0.785 mmol) in methylene chloride (3.5 ml) was added oxalyl chloride (101.0 μl, 1.178 mmol) under stirring at −15° C. The reaction mixture was stirred for 2.5 hours at room temperature and then distilled under reduced pressure to remove the solvent. The residue was dissolved in methylene chloride (3.5 ml), followed by the addition of a solution of methyl 3-chloro-4-aminophenylacetate (164.6 mg, 0.824 mmol) in methylene chloride (3.5 ml) and triethylamine (0.35 ml, 2.474 mmol) under stirring at room temperature. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then distilled under reduced pressure to remove the solvent. The residue was dissolved in chloroform. The resulting solution was washed successively with 1N HCl and saturated saline, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 3-chloro-4-((1-isopropyl-3-indolylcarbonyl)amino)phenylacetate (275.3 mg, 91%) was obtained as a brown solid. The resulting compound was provided for the subsequent reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 2.5 hours at room temperature
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in methylene chloride (3.5 ml)
  5. stirringunder stirring at room temperature
  6. stirringThe reaction mixture was stirred at room temperature for 18 hours
  7. distillationThe reaction mixture was then distilled under reduced pressure
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in chloroform
  10. washThe resulting solution was washed successively with 1N HCl and saturated saline
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationdistilled under reduced pressure
  13. customto remove the solvent

Sources & evidence

ORD record
ord-28a15cc33ce24a83bd6f3fa4421543fa
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…