HCID 86712756, compound → HCID 86712758, compound

HRID 1754548Notes

Reaction equation

HRID 1754548 reaction equation
[C:1]1(=[CH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1>[F:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]2[C:10]=1[C:1]1([CH2:4][CH2:3][CH2:2]1)[CH2:5][C:6](=[O:7])[NH:8]2

Participants

3

Reactant 1

HCID 86712756HCID 86712756, compound

Product 1

HCID 86712758HCID 86712758, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 400 mg (1.94 mmol) of 2-cyclobutylidene-N-(3-fluorophenyl)-acetamide obtained in step 31.1 was dissolved in 19.5 ml of toluene and irradiated with a Hg middle pressure lamp in a suitable device till completion of the reaction indicated by liquid chromatography. The crude solution was concentrated in vacuo and the residue was purified by column chromatography on silica (eluent: 10-30% ethyl acetate in heptane) to yield 55 mg (14%) of the title compound as a beige solid.

Workup

  1. customirradiated with a Hg middle pressure lamp in a suitable device till completion of the reaction
  2. concentrationThe crude solution was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica (eluent: 10-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-05c45e43f2ff46c5bd15717a14a8811c
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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