Triethylamine → HCID 68918949, compound

HRID 2111637Notes

Reaction equation

HRID 2111637 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][CH2:20][OH:21].[C:22](Cl)(=[O:25])[CH2:23][CH3:24].C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][CH2:20][O:21][C:22]([CH2:23][CH3:24])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 23084549HCID 23084549, compound

Product 1

HCID 68918949HCID 68918949, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5,6-dimethyl-2-(3-pyridyl)-3-(2-hydroxyethyl)isoindolin-1-one (50 mg, 0.18 mmol), propionyl chloride (16 mg, 0.18 mmol) and triethylamine (18 mg, 0.18 mmol) in dichlorometane was stirred at 25° C. for 3 hrs. The reaction solution was washed with water, dried, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=20:1) to give 43 mg of the title compound.

Workup

  1. washThe reaction solution was washed with water
  2. customdried
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe residue was purified by silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-88cc735ca1e746ada6a3483a5c347438
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

Loading…