Acetic Acid → HCID 69584053, compound

HRID 1826761Notes

Reaction equation

HRID 1826761 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)[CH2:3][CH2:2]1.[CH:17]([C:19]1[NH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:27]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=O.N1CCCC1.C(O)(=O)C>C(O)C>[O:16]=[C:10]1[C:9](=[CH:17][C:19]2[NH:20][C:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=3[C:27]=2[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH:4]2[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]2)[NH:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acidHCID 221353964-(Piperidin-4-yl)indolin-2-one

Product 1

HCID 69584053HCID 69584053, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-piperidin-4-yl-1,3-dihydroindol-2-one (45 mg, 0.2 mmol), 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (57 mg, 0.23 mmol) and pyrrolidine (0.3 mL) in ethanol (0.5 mL) was heated to reflux for 2 hours. Acetic acid (0.05 mL) was added to the reaction and heating was continued for another 10 minutes. The reaction was cooled and the precipitate which formed was collected by vacuum filtration, washed with ethanol and dried to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureheating
  4. temperatureThe reaction was cooled
  5. customthe precipitate which formed
  6. filtrationwas collected by vacuum filtration
  7. washwashed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-13bc7a50860f4f349447a94290ec4c12
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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