1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69209226, compound

HRID 30712Notes

Reaction equation

HRID 30712 reaction equation
C([O:3][C:4]([O:6][CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:35])/[CH:20]=[CH:21]/[C:22]2[CH:23]=[N:24][N:25]([CH3:34])[C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:14][CH:13]=1)[C:8]([NH2:10])=[O:9])=O)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[O:3]=[C:4]1[NH:10][C:8](=[O:9])[CH:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:35])/[CH:20]=[CH:21]/[C:22]3[CH:23]=[N:24][N:25]([CH3:34])[C:26]=3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:16][CH:17]=2)[O:6]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69207807HCID 69207807, compound

Product 1

HCID 69209226HCID 69209226, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(ethoxycarbonyloxy)-3-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-2-propenoyl}amino)phenyl]propionamide (420 mg), 1,8-diazabicyclo[5.4.0]-7-undecene (266 mg) and acetonitrile (10 ml) was stirred at room temperature for 1 hr. The reaction mixture was concentrated and diluted with ethyl acetate. The mixture was successively washed with a 1N aqueous hydrochloric acid solution, water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give (2E)-N-{4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenyl}-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide (293 mg, 77%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe mixture was successively washed with a 1N aqueous hydrochloric acid solution, water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-527e172b86f1468aac7c4120d94e5520
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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