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Water → 3-(Methylthio)-N-[[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]propanamide

HRID 499475
Notes
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Reaction equation

HRID 499475 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.CCC[C:30](Cl)=[S:31].[C:33](OCC)(=O)C.O>CN(C)C(=O)C>[CH3:33][S:31][CH2:30][CH2:2][C:3]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[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)[N:15]=1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22343826Butanecarbothioyl chlorideHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 597503853-(Methylthio)-N-[[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]propanamideYield 24%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.80 g, 2.1 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and 3-methylthiopropionyl chloride (0.86 g, 6.2 mmol) was added thereto. The reaction mixture was stirred at 60° C. for 15 hrs and 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 methanol-ethyl acetate (1:10, v/v) were collected, concentrated and recrystallized from diisopropyl ether-tetrahydrofuran to give the titled compound (0.18 g, 24%) 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 diisopropyl ether-tetrahydrofuran

Sources & evidence

ORD record
ord-67bf563eaca540309af72a340568e8a2
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767665B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes