1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178419306, compound

HRID 2246616Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)=[N:9][NH:10]C(OC(C)(C)C)=O)=[C:4](F)[CH:3]=1.N12CCCN=C1CCCCC2>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:8]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)=[N:9][NH:10]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1,1-dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylate (Intermediate 8, 1.1 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (424 μL) in tetrahydrofuran (12 mL) in a sealed vial was heated in a microwave oven at 150° C. for 30 min. The reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL) and the organic layer was dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by chromatography on a silica column, eluting with a cyclohexane:ethyl acetate gradient, to give the title compound as a colourless glass (405 mg).

Workup

customThe reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL)
customthe organic layer was dried
concentrationconcentrated under vacuum
customThe residue was purified by chromatography on a silica column
washeluting with a cyclohexane

Sources & evidence

ORD record: ord-034bdf1948b0458a8404be38db15ffde
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687532B2

Reaction notes

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