Diethylamine → HCID 178418727, compound

HRID 1884416Notes

Reaction equation

HRID 1884416 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]=[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])=[CH:9][CH:8]=1.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>CO>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]=[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])=[CH:9][CH:8]=1)[CH3:26]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178418946HCID 178418946, compound

Product 1

HCID 178418727HCID 178418727, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 25 mL pressure tube is charged with 3-{[4-(4-Iodo-butoxy)-phenylamino]-methylene}-1,3-dihydro-indol-2-one (75 mg, 0.173 mmol), diethylamine (2 mL) and the reaction mixture is heated at 50° C. for 3 h. The reaction mixture is cooled to room temperature and partitioned between EtOAc and H2O. The organic layer is washed with saturated aqueous NaHCO3 solution, brine, and dried over anhydrous Na2SO4. The organic layer is collected by filtration and concentrated to give a yellow solid. The solid is broken up in MeOH and collected by filtration to give the named compound as a yellow solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. custompartitioned between EtOAc and H2O
  3. washThe organic layer is washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe organic layer is collected by filtration
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e025071d146549f2aba3cbf171d39c84
Source dataset
uspto-grants-2004_07
Patent number
US06765012B2

Reaction notes

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