1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19357176, compound

HRID 377905Notes

Reaction equation

HRID 377905 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[C:15]([NH:17][C:18](=[O:26])OC3C=CC=CC=3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1.[CH3:27][C:28]1[CH:29]=[C:30]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:31]=[C:32]([CH3:34])[CH:33]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[C:15]([NH:17][C:18]([N:38]3[CH2:39][CH2:40][N:35]([C:30]4[CH:31]=[C:32]([CH3:34])[CH:33]=[C:28]([CH3:27])[CH:29]=4)[CH2:36][CH2:37]3)=[O:26])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27586261-(3,5-Dimethylphenyl)piperazineHCID 53775163HCID 53775163, compound

Product 1

HCID 19357176HCID 19357176, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-[2-(pyridin-3-yl)quinolin-4-yl]carbamate(171 mg, 0.5 mmol) and 1-(3,5-dimethylphenyl)piperazine(95 mg, 0.5 mmol) were dissolved in anhydrous tetrahydrofuran and DBU(117 mg, 0.75 mmol) was added. The resulting mixture was stirred at room temperature for 2 hours, concentrated under the reduced pressure to remove tetrahydrofuran, and purified by column chromatography(ethylacetate:hexane=1:1) to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove tetrahydrofuran
  3. custompurified by column chromatography(ethylacetate:hexane=1:1)

Sources & evidence

ORD record
ord-7ee94e9f8cc641918413c9c294c6d47d
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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