HCID 10314617, compound → HCID 10040744, compound

HRID 2256407Notes

Reaction equation

HRID 2256407 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[C:13]([F:24])[CH:12]=2)[CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]([F:24])[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[C:15]([F:17])[CH:16]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 10314617HCID 10314617, compound

Product 1

HCID 10040744HCID 10040744, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-5-(Azidomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (PREPARATION 6, 354 mg, ~1.07 mmol) in methanol (40 ml) and palladium on carbon (10%, 50 mg) are mixed. The mixture is purged with nitrogen and then placed under an atmosphere of hydrogen (1 atm). The reaction is allowed to stir at 20°-25° for 16 hrs. After this time, the reaction is filtered and concentrated under reduced pressure to a solid amine. The crude amine is suitable for acetylation without further purification. An analytical sample is prepared by preparative TLC (SG) methanol/chloroform (10/90). The title compound is recovered as a solid, mp 143°-145°; FTIR (neat) cm-1 3368, 1757, 1646, 1412, 1244, 1025 and 714; MS (EI, m/z) 305, 276, 233, 219, 44 and 29; NMR (CDCl3) 8.71, 8.62, 7.79, 7.39, 7.33, 4.79-4.70, 4.06, 3.92, 3.18, 2.98 and 1.52 δ.

Workup

  1. customThe mixture is purged with nitrogen
  2. filtrationAfter this time, the reaction is filtered
  3. concentrationconcentrated under reduced pressure to a solid amine
  4. customThe crude amine is suitable for acetylation without further purification
  5. customAn analytical sample is prepared by preparative TLC (SG) methanol/chloroform (10/90)
  6. customThe title compound is recovered as a solid, mp 143°-145°

Sources & evidence

ORD record
ord-611cf1f694424d50a5f731b481c92694
Source dataset
uspto-grants-1997_08
Patent number
US05654435

Reaction notes

Loading…