Pyridine → HCID 90023600, compound

HRID 56253Notes

Reaction equation

HRID 56253 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[C:5](\[NH2:7])/[CH3:6].N1C=CC=CC=1.[F:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[O:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]([CH:26]=[CH:27][CH:28]=1)[O:19][CH2:20][CH2:21][CH2:22][C:23]([NH:7]/[C:5](/[CH3:6])=[CH:4]\[C:3]([O:2][CH3:1])=[O:8])=[O:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 643918Methyl 3-aminocrotonateHCID 900231674-(3-Fluorophenoxy)butanoyl chloride

Product 1

HCID 90023600HCID 90023600, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (Z)-methyl-3-aminobut-2-enoate (1.70 g, 14.8 mmol) and pyridine (1.20 g, 15.2 mmol) in DCM (25 mL) was added a solution of 4-(3-fluorophenoxy)butanoyl chloride (3.28 g, 15.1 mmol) in DCM (5 mL) with stirring and the mixture was stirred for 1 h. It was then washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1) to give the title compound as a white solid (1.20 g, 28%).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. washIt was then washed with brine (50 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1)

Sources & evidence

ORD record
ord-32925e870b8c41ae88ce10eab7d522d9
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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