1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23121848, compound

HRID 1713561Notes

Reaction equation

HRID 1713561 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N12CCCN=C1CCCCC2.ClC(Cl)(Cl)[C:36]([NH:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][CH:43]=[N:44]2)=[O:37]>C(#N)C.O>[O:16]=[C:9]1[N:10]2[CH2:15][CH2:14][N:13]([C:36]([NH:38][C:39]3[CH:48]=[CH:47][CH:46]=[C:45]4[C:40]=3[CH:41]=[CH:42][CH:43]=[N:44]4)=[O:37])[CH2:12][CH:11]2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:8]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9524932,2,2-trichloro-N-5-quinolinylacetamideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121848HCID 23121848, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.19 g, 1.3 mmol) in acetonitrile (6 mL) was added 2,2,2-trichloro-N-(5-quinolinyl)acetamide (0.16 g, 0.55 mmol), and the mixture was heated under reflux for 6 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed twice with water, once with saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate), and then recrystallized from hexane-ethyl acetate to obtain the title compound (78 mg, yield 33%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed twice with water, once with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solid was filtered off
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  9. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a01d84f601774d0e94e21ca31f76ba26
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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