Triethylamine → HCID 73427145, compound

HRID 1507552Notes

Reaction equation

HRID 1507552 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>ClCCl.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:10]=2)[C:6]([CH3:14])([CH3:13])[C:7]1=[O:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 529112486-Amino-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 73427145HCID 73427145, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 6-amino-1,3,3-trimethylindolin-2-one (W. von der Saal et al., J. Med. Chem. 1989, 32(7), 1481-1491; 500 mg, 2.63 mmol) in dry dichloromethane (13 ml) were added triethylamine (798 mg, 1.1 ml, 7.88 mmol) and isonicotinoyl chloride hydrochloride (724 mg, 3.94 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with dichloromethane, water and 1 M aqueous sodium carbonate solution. The aqueous phase was extracted with dichloromethane. The combined organic layers were washed with 1 M aqueous sodium carbonate solution, dried over sodium sulfate, the solvent was evaporated and the residue was purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as brown solid (661 mg).

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane
  2. washThe combined organic layers were washed with 1 M aqueous sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b322486c67cb46bab8a256180065cd97
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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