Pyridine → HCID 76741052, compound

HRID 2368835Notes

Reaction equation

HRID 2368835 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.[NH2:22][OH:23].N1C=CC=CC=1>C(O)C>[N:1]1([C:10]2[S:14][C:13]([C:15](=[N:22][OH:23])[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

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 58284825HCID 58284825, compound

Product 1

HCID 76741052HCID 76741052, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of compound (84) (0.703 mmoles) in ethanol (10 ml) was added hydroxylamine HCl (2.878 mmoels) and pyridine (2.844 mmoles) at ambient temp. The reaction 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 (86 & 87).

Workup

  1. temperatureThe reaction 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-8bd548eb89d541d2afc172413a7f80d8
Source dataset
uspto-grants-2014_04
Patent number
US08703811B2

Reaction notes

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