Hydrazine → HCID 89813510, compound

HRID 525385Notes

Reaction equation

HRID 525385 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[O:10][C:9]2=[O:21])[CH:5]=[CH:4][N:3]=1.[NH2:22][NH2:23]>>[NH:22]([C:2]1[CH:7]=[C:6]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[O:10][C:9]2=[O:21])[CH:5]=[CH:4][N:3]=1)[NH2:23]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 89813682HCID 89813682, compound

Product 1

HCID 89813510HCID 89813510, compound

Conditions

Temperature
140 °C

Procedure

A mixture of (S)-3-(2-chloropyridin-4-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (1.44 g, 4.76 mmol) and anhydrous hydrazine (7.46 mL, 238 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) was heated at 140° C. for 15 minutes. LC-MS indicated complete consumption of starting material with the desired product as the major product. After cooling to room temperature, the solution was concentrated under reduced pressure. The residue thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 10% MeOH in DCM, to provide (S)-3-(2-hydrazinylpyridin-4-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one. m/z (ESI) 299.2 (M+H)+.

Workup

  1. customconsumption of starting material with the desired product as the major product
  2. temperatureAfter cooling to room temperature
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas absorbed onto a plug of silica gel
  6. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  7. washeluting with a gradient of 0% to 10% MeOH in DCM

Sources & evidence

ORD record
ord-e83baa2ff756446bb3dac6fd616f7f23
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…