Pyridine → HCID 9863078, compound

HRID 583569Notes

Reaction equation

HRID 583569 reaction equation
[NH2:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([F:22])[CH:10]=2)[CH2:4]1.N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(Cl)Cl>[C:29]([NH:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]([F:22])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:13]([F:15])[CH:14]=2)[CH2:4]1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10040744HCID 10040744, compound

Product 1

HCID 9863078HCID 9863078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(±)-5-(Aminomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (PREPARATION 7, 135 mg, 0.433 mmol) in anhydrous methylene chloride (10 ml), pyridine (143 μl, 1.77 mmol, 4 eq) and acetic anhydride (167 μl, 1.77 mmol, 4 eq) are combined. The reaction is allowed to stir at 20-25° under nitrogen. After 2.5 hr the reaction is added to methylene chloride (30 ml) and washed with saturated sodium bicarbonate then brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to a solid. This material is purified by silica gel (70 g) chromatography eluted with methanol/chloroform (1/99-4/96 gradient). The appropriate fractions are pooled and concentrated to give the title compound, mp 218-219°; FTIR (mull) cm-1 3347, 1742, 1679, 1648, 1563, 1409, 1247, 1022, 755; MS (EI, m/z) 347 [M+ ], 303, 275, 244, 219, 73, 56; NMR (CDCl3) 8.68, 8.59, 7.85, 7.48-7.41, 7.31, 4.87-4.79, 4.10, 3.82, 3.72-3.57, 2.03 δ.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialbrine, dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a solid
  5. customThis material is purified by silica gel (70 g) chromatography
  6. washeluted with methanol/chloroform (1/99-4/96 gradient)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f3a9c105b76b423fbbd18b4b717127bd
Source dataset
uspto-grants-1999_07
Patent number
US05929248

Reaction notes

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