Cesium carbonate → HCID 72702970, compound

HRID 1777396Notes

Reaction equation

HRID 1777396 reaction equation
O[CH2:2][C@H:3]1[N:7]([C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)=[O:9])[CH2:6][C@H:5]([CH3:22])[O:4]1.CS(Cl)(=O)=O.[F:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:36]=[N:37][NH:38][CH:39]=2)=[N:33][CH:34]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)(Cl)Cl.O>[F:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:39]=[N:38][N:37]([CH2:2][C@H:3]3[N:7]([C:8]([C:10]4[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=4[N:17]4[N:18]=[CH:19][CH:20]=[N:21]4)=[O:9])[CH2:6][C@H:5]([CH3:22])[O:4]3)[CH:36]=2)=[N:33][CH:34]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 67991756HCID 67991756, compoundHCID 118020591HCID 118020591, compound

Product 1

HCID 72702970HCID 72702970, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

By using ethyl(2RS,5S)-5-methyl-3-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,3-oxazolidine-2-carboxylate obtained in Reference Example 5 (0.11 g, 0.33 mmol) as the raw material, the same procedure as in Reference Example 2 was carried out to obtain the diastereomer mixture of [2-(hydroxymethyl)-5-methyl-1,3-oxazolidin-3-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (colorless oil). The obtained diastereomer mixture was purified by thin layer chromatography (1 mm, hexane/EtOAc=50/50) to obtain [(2S,5S)-2-(hydroxymethyl)-5-methyl-1,3-oxazolidin-3-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (colorless oil). To a solution of the obtained [(2S,5S)-2-(hydroxymethyl)-5-methyl-1,3-oxazolidin-3-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (30.2 mg, 0.10 mmol) and TEA (0.021 mL, 0.15 mmol) in CHCl3 (0.8 mL), MsCl (0.011 mL, 0.15 mmol) were added under cooling with ice water and the resulting mixture was stirred for 1 hour. Water was added to the reaction mixture under cooling with ice water, followed by extraction with CHCl3. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over Na2SO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. 5-Fluoro-2-(1H-pyrazol-4-yl)pyridine (0.033 g, 0.20 mmol) and Cs2CO3 (0.065 g, 0.20 mmol) were added to a solution of the obtained residue (0.5 mL). The resulting mixture was reacted for 1 hour at 120° C. under irradiation of microwave. The reaction mixture was allowed to cool, water was added thereto, followed by extraction with CHCl3, the extract was passed through an ISOLUTE Phase Separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by HPLC to obtain the title compound (0.020 g) (colorless oil).

Workup

  1. extractionfollowed by extraction with CHCl3
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over Na2SO4
  4. filtrationthe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting mixture was reacted for 1 hour at 120° C. under irradiation of microwave
  7. temperatureto cool
  8. extractionfollowed by extraction with CHCl3
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by HPLC

Sources & evidence

ORD record
ord-f0dbeb2625284440be7ed87f797e236f
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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