Pyridine → HCID 18670713, compound

HRID 1059422Notes

Reaction equation

HRID 1059422 reaction equation
COC[N:4]1[C:9]2[CH:10]=[C:11]([C:14]3[S:15][CH2:16][CH:17](O)[N:18]=3)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:20]=[CH:21][CH:22]=[N:23][C:5]1=2.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>COCCOC.C(OCC)(=O)C>[S:15]1[CH:16]=[CH:17][N:18]=[C:14]1[C:11]1[CH:12]=[CH:13][C:8]2[S:7][C:6]3[N:20]=[CH:21][CH:22]=[N:23][C:5]=3[NH:4][C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 18670429HCID 18670429, compound

Product 1

HCID 18670713HCID 18670713, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

450 mg of 2-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)-4,5-dihydro-1,3-thiazol-4-ol and 0.83 ml of pyridine were dissolved in 15 ml of 1,2-dimethoxyethane. While stirring the reaction mixture under ice-cooling, 300 mg of trifluoroacetic anhydride was dropped thereinto and the resulting mixture was stirred for 1 hour. Then the reaction mixture was distributed into an aqueous solution of sodium bicarbonate and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the oily residue thus obtained was treated in the same manner as the one of Example 434 and purified by silica gel column chromatography (eluted with dichloromethane/methanol). Thus 230 mg of the title compound was obtained as yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred for 1 hour
  3. extractionThe organic layer was extracted
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe oily residue thus obtained
  8. additionwas treated in the same manner as the one of Example 434
  9. custompurified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-c12a9439145141a2ac22ce67369b4254
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…