Ethanesulfonyl chloride → HCID 59750102, compound

HRID 499477Notes

Reaction equation

HRID 499477 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[O:22]=[C:20]1[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[S:17][C:16]([C:14]2[N:15]=[C:10]([CH2:9][NH:8][S:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH:11]=[CH:12][CH:13]=2)=[N:21]1

Participants

6

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750102HCID 59750102, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (500 mg, 1.3 mmol) and ethanesulfonyl chloride (270 mg, 2.1 mmol) were dissolved in ethyl acetate (10 ml) and water (5 ml), and sodium hydrogen carbonate (270 mg, 3.2 mmol) was added thereto. The mixture was stirred at room temperature for 3 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (2:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (101 mg, 21%) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with ethyl acetate-hexane (2:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-edf8ed2614b34ccab0e8b43fff8de5f0
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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