Potassium Carbonate → HCID 57948953, compound

HRID 1992277Notes

Reaction equation

HRID 1992277 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([C@:14]3([CH3:24])[CH2:19][CH2:18][S:17][C:16]([NH:20]C(=O)C)=[N:15]3)[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO.CO.O>[F:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([C@:14]3([CH3:24])[CH2:19][CH2:18][S:17][C:16]([NH2:20])=[N:15]3)[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68540382HCID 68540382, compound

Product 1

HCID 57948953HCID 57948953, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (S)-N-(4-(3-(2-fluoropyridin-3-yl)phenyl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)acetamide (450 mg, 1.3 mmoles) in methanol (40 mL) is added a solution of K2CO3 (210 mg, 1.5 mmoles) in methanol:water (2:1, 15 mL). The reaction is stirred at room temperature for 6 h. The solvent is removed under reduced pressure and the residue is dissolved in ethyl acetate. The ethyl acetate layer is washed with water and saturated aqueous NaCl, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue is purified by using SCX column chromatography to give the title compound (65% yield): MS (m/z): 302 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washThe ethyl acetate layer is washed with water and saturated aqueous NaCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. customThe residue is purified

Sources & evidence

ORD record
ord-1e55957ba08c482cb94777ee0bcdd2bc
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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