Pyridine → HCID 68673471, compound

HRID 1927654Notes

Reaction equation

HRID 1927654 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]([NH:9][NH:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)=O)[CH3:2].N1C=CC=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1[O:20][C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)=[N:10][N:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 68674595HCID 68674595, compound

Product 1

HCID 68673471HCID 68673471, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[N′-(3,4-difluorobenzoyl)hydrazino]-4-oxo-butyric acid ethyl ester (590 mg, 1.96 mmol) and pyridine (474 μL, 5.88 mmol) in methylene chloride (25 mL) at −78° C. was added dropwise triflic anhydride (397 μL, 2.35 mmol) and the reaction was allowed to warm up to rt overnight. The reaction mixture was diluted with methylene chloride (100 mL), washed with 0.1 M HCl and brine, dried over sodium sulfate and concentrated to provide 3-[5-(3,4-difluorophenyl)-[1,3,4]oxadiazol-2-yl]propionic acid ethyl ester. 1H NMR (300 MHz, CDCl3) δ 7.89-7.77 (m, 2H), 7.31 (m, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.24 (t, J=7.2 Hz, 2H), 2.92 (t, J=7.4 Hz, 2H), 1.27 (t, J=7.1 Hz, 3H).

Workup

  1. washwashed with 0.1 M HCl and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9b229474079b406d81a33bdc5b4bc721
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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