1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 136621538, compound

HRID 705343Notes

Reaction equation

HRID 705343 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19](=[N:21][OH:22])[NH2:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[C:38](C1NC=CN=1)(C1NC=CN=1)=[O:39].N12CCCN=C1CCCCC2>O1CCOCC1>[CH:1]1([C:4]2[C:5]([N:24]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[S:25]([CH3:28])(=[O:26])=[O:27])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][C:38](=[O:39])[O:22][N:21]=4)[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86710151HCID 86710151, compound

Product 1

HCID 136621538HCID 136621538, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 8C (2.62 g, 5.0 mmol), carbonyl diimidazole (0.973 g, 6.00 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.829 mL, 5.50 mmol) in dioxane (20 mL) was refluxed for one hour, cooled and partitioned between ethyl acetate and 1 M aqueous HCl. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was triturated with ethyl acetate/hexane (1:3) to give the title compound as a solid (2.19 g, 80%).

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and 1 M aqueous HCl
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-cc4f2bcbb7224a5c8e2ac3832cabca2a
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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