1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 118023425, compound

HRID 929300Notes

Reaction equation

HRID 929300 reaction equation
[C:1]([NH:4][C@H:5]1[CH2:9][C@@H:8]([C:10]([N:12]([C:14]2[C:15]([Cl:25])=[N:16][N:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:18]=2)[CH3:13])=[O:11])[CH:7]=[CH:6]1)(=[O:3])[CH3:2].N12CCCN=C1CCCCC2>CS(C)=O.[NH4+].[Cl-]>[C:1]([NH:4][C@H:5]1[CH2:9][C:8]([C:10]([N:12]([C:14]2[C:15]([Cl:25])=[N:16][N:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:18]=2)[CH3:13])=[O:11])=[CH:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118023538HCID 118023538, compound

Product 1

HCID 118023425HCID 118023425, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (1R,4S)-4-acetamido-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-methyl-cyclopent-2-enecarboxamide (0.230 g, 0.639 mmol) dissolved in dimethylsulfoxide (DMSO, 10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 4.00 mL, 26.7 mmol). After stirring for 4 hours at a temperature of 100° C., the reaction was cooled and diluted with saturated aqueous NH4Cl (200 mL) and extracted with EtOAc. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluting with MeOH/CH2Cl2 to provide the title compound F41 as a yellow oil (0.120 g, 44%).

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluting with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-78a4e588ead5414e93ab5a0d8a3df784
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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