Pyridine → HCID 76741051, compound

HRID 2368836Notes

Reaction equation

HRID 2368836 reaction equation
[N:1]1([C:10]2[S:14][C:13]([C:15](=O)[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Cl.[CH3:22][O:23][NH2:24].N1C=CC=CC=1>C(O)C>[CH3:22][O:23][N:24]=[C:15]([C:13]1[S:14][C:10]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)=[CH:11][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 58284825HCID 58284825, compound

Product 1

HCID 76741051HCID 76741051, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of compound (84) (0.703 mmoles) in Ethanol (10 ml) was added N-methoxy amine HCl (2.878 m.moles) and Pyridine (2.844 m.moles) at ambient temp. The reaction mass was heated to reflux for 2.0 hrs. After completion of reaction, distilled off the solvent completely, added Water (20 ml) and the product was extracted in ethyl acetate (2×100 ml), washed with 10% brine and dried over sodium sulphate. The solvent was distilled completely under reduced pressure to get the crude compound. This crude compound was purified by preparative HPLC to get the pure isomers (88 & 89).

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureto reflux for 2.0 hrs
  3. customAfter completion of reaction
  4. distillationdistilled off the solvent completely
  5. additionadded Water (20 ml)
  6. extractionthe product was extracted in ethyl acetate (2×100 ml)
  7. washwashed with 10% brine
  8. dry with materialdried over sodium sulphate
  9. distillationThe solvent was distilled completely under reduced pressure

Sources & evidence

ORD record
ord-c9bf9fe7180544ae932112bb9a3da3e7
Source dataset
uspto-grants-2014_04
Patent number
US08703811B2

Reaction notes

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