Triethylamine → HCID 69659243, compound

HRID 1829070Notes

Reaction equation

HRID 1829070 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([OH:23])=O)[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C([N:26](CC)CC)C.ClCCOC=O.[NH4+].[OH-]>C1COCC1>[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([NH2:26])=[O:23])[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 2467482-Chloroethyl formateHCID 69659233HCID 69659233, compound

Product 1

HCID 69659243HCID 69659243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (100 mg, 0.325 mmol) and triethylamine (58.9 μl, 0.423 mmol) in THF (3.0 ml) was added chloroethylformate (35.7 μl, 0.374 mmol). The mixture was stirred at room temperature for 25 minutes, and then concentrated NH4OH (3.0 ml) was added. After stirring for 8 minutes at room temperature, the reaction was partitioned between 4% HCl aqueous solution, and EtOAc. The organic layer was then washed with saturated NaHCO3 aqueous solution, water, dilute HCl aqueous solution, brine, dried with anhydrous Na2SO4 and rotary evaporated to yield a solid. The solid was recrystallized from CHCl3/MeOH to give 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetamide as a yellow-gold solid (34.4 mg, 35%).

Workup

  1. stirringAfter stirring for 8 minutes at room temperature
  2. customthe reaction was partitioned between 4% HCl aqueous solution, and EtOAc
  3. washThe organic layer was then washed with saturated NaHCO3 aqueous solution, water, dilute HCl aqueous solution, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customrotary evaporated
  6. customto yield a solid
  7. customThe solid was recrystallized from CHCl3/MeOH

Sources & evidence

ORD record
ord-b94edbea4cc44a7b9aa9e3e7c8cb7af4
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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