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Triethylamine → (4S,5R)-3-{[3-bromo-6-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1508592
Notes
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Reaction equation

HRID 1508592 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][N:10]2[C@@H:14]([CH3:15])[C@@H:13]([C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=3)[O:12][C:11]2=[O:27])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.Cl.[F:29][C:30]1([F:34])[CH2:33][NH:32][CH2:31]1.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[C:3]([CH2:9][N:10]2[C@@H:14]([CH3:15])[C@@H:13]([C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=3)[O:12][C:11]2=[O:27])=[N:4][C:5]([N:32]2[CH2:33][C:30]([F:34])([F:29])[CH2:31]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 86704638(4S,5R)-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 86704639(4S,5R)-3-{[3-bromo-6-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4S,5R)-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (1.0721 g, 2.293 mmol), 3,3-difluoroazetidine hydrochloride (1.336 g, 10.32 mmol), triethylamine (3.20 ml, 22.93 mmol) and THF (10 ml) were sealed in a microwave vessel and subject to microwave irradiation at 150° C. for 8 hrs. Volatiles were removed under reduced pressure. The resulting pot residue was worked up with brine/ethyl acetate. The combined extracts were dried over Na2SO4, filtered and evaporated to afford a dark mixture. This dark mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge). The column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate). Related fractions were pooled and evaporated under reduced pressure to afford a light amber glass of 530.8 mg as the titled compound. LCMS calc.=523.03. found=525.99.

Workup

  1. customsubject to microwave irradiation at 150° C. for 8 hrs
  2. customVolatiles were removed under reduced pressure
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a dark mixture
  7. customThis dark mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge)
  8. washThe column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0f3bf028526340709b385917049e6aa0
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221834B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes