1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66953497, compound

HRID 2096976Notes

Reaction equation

HRID 2096976 reaction equation
[CH:1]1([NH:4][C:5](=[N:14][OH:15])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[C:7]=2F)[CH2:3][CH2:2]1.N12CCCN=C1CCCCC2>O1CCCC1>[CH:1]1([NH:4][C:5]2[C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[C:7]=3[O:15][N:14]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178526351HCID 178526351, compound

Product 1

HCID 66953497HCID 66953497, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-cyclopropyl-2-fluoro-N′-hydroxy-3-iodobenzimidamide (preparation 22f, 2.15 g, 8.1 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.30 mL, 8.7 mmol) in tetrahydrofuran (13 mL) was heated at 150° C. for 150 minutes in Biotage Initiator Microwave Synthesizer. Then, the mixture was cooled to ambient temperature and evaporated. The residue was partitioned between water and ethyl acetate and the organic layer was washed with brine, dried (MgSO4) and evaporated. The crude residue was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title compound (1.61 g, 68%) as a white solid.

Workup

  1. temperatureThen, the mixture was cooled to ambient temperature
  2. customevaporated
  3. customThe residue was partitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-51acdf50eef24b25b295d28b4b8ac313
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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