Acetyl chloride → N-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]acetamide

HRID 499469Notes

Reaction equation

HRID 499469 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=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.C(Cl)(=O)C.C(OCC)(=O)C.O1CCCC1>CN(C)C(=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][C:3](=[O:5])[CH3:2])[CH:11]=[CH:12][CH:13]=2)=[N:21]1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750356N-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]acetamideYield 28.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (350 mg, 0.91 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and acetyl chloride (150 mg, 1.91 mmol) was added thereto. The reaction mixture was stirred at 60° C. for 3 hrs and combined with ethyl acetate, tetrahydrofuran 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 methanol-ethyl acetate (1:10, v/v) were collected, concentrated and recrystallized from methanol-diisopropyl ether to give the titled compound (81 mg, 28%) as white 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 methanol-ethyl acetate (1:10
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-a7112b6f33a240d1a7703b88b9d4909a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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