Piperidine → (Z)-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-6,7,8,9-tetrahydro-1H,5H-1,5-diaza-cyclopentacycloocten-4-one

HRID 2191500Notes

Reaction equation

HRID 2191500 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][N:6]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2[NH:14][C:15]([CH:18]=O)=[C:16]([CH3:17])[C:8]=2[C:7]1=[O:20])[CH3:2].[F:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27]2.N1CCCCC1>C(O)C>[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][N:6]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2[NH:14][C:15](/[CH:18]=[C:27]3\[C:28](=[O:33])[NH:29][C:30]4[C:26]\3=[CH:25][C:24]([F:23])=[CH:32][CH:31]=4)=[C:16]([CH3:17])[C:8]=2[C:7]1=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 498404665-(2-diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7,8,9-hexahydro-1H-1,5-diaza-cyclopentacyclooctene-2-carbaldehyde

Product 1

HCID 49840467(Z)-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-6,7,8,9-tetrahydro-1H,5H-1,5-diaza-cyclopentacycloocten-4-oneYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Diethylamino-ethyl)-3-methyl-4-oxo-4,5,6,7,8,9-hexahydro-1H-1,5-diaz a-cyclopentacyclooctene-2-carbaldehyde 60e (20 mg, 0.066 mmol) was dissolved in 1 ml of ethanol under stirring, and added with 5-fluoro-1,3-dihydro-indol-2-one (9.9 mg, 0.066 mmol) to the solution at room temperature. The reaction mixture was stirred in dark until dissolved, added with 0.1 ml of piperidine, and heated to reflux for 2 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, filtered to obtain the title compound (Z)-5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-6,7,8,9-tetrahydro-1H,5H-1,5-diaza-cyclopentacycloocten-4-one 60 (14 mg, yield 48.8%) as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred in dark
  2. dissolutionuntil dissolved
  3. temperatureheated
  4. temperatureto reflux for 2 hours
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c87cbd306614499f8667af3003cec2b1
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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