HCID 9926167, compound → HCID 54373932, compound

HRID 2120255Notes

Reaction equation

HRID 2120255 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[O:7][CH2:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][C:13](=[O:19])[NH:14]2)([CH3:3])[CH3:2].[CH3:23][N:24]([CH3:37])[CH2:25][CH2:26][CH2:27][C:28]1[C:29]([CH3:36])=[C:30]([CH:34]=O)[NH:31][C:32]=1[CH3:33]>N1CCCC1.C(O)C>[CH3:37][N:24]([CH3:23])[CH2:25][CH2:26][CH2:27][C:28]1[C:29]([CH3:36])=[C:30]([CH:34]=[C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[CH:18][C:10]=3[CH2:9][CH2:8][O:7][C:6]3[CH:20]=[CH:21][CH:22]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=3)[NH:14][C:13]2=[O:19])[NH:31][C:32]=1[CH3:33]

Participants

5

Reactant 2

HCID 9926167HCID 9926167, compoundHCID 219257584-(3-dimethylaminopropyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 54373932HCID 54373932, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 31268PyrrolidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[2-(3-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one (28 mg, 0.095 mmol), 4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (20 mg, 0.095 mmol) and 1 drop of pyrrolidine in 1.0 mL of ethanol was heated at 90° C. for 4 hours and cooled to room temperature. The precipitate was filtered, washed with cold ethanol and hexane, and dried in a vacuum oven overnight to give 40 mg (87%) of 3-[4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-[2-(3-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with cold ethanol and hexane
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-6f856657282a47ad85a1794083f08c0c
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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