Potassium Carbonate → HCID 59750401, compound

HRID 748297Notes

Reaction equation

HRID 748297 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.[P:27](Cl)([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[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][P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])[CH:11]=[CH:12][CH:13]=2)=[N:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750401HCID 59750401, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (400 mg, 1.0 mmol) and diethyl chlorophosphate (360 mg, 2.1 mmol) were dissolved in acetonitrile (15 ml), and potassium carbonate (430 mg, 3.1 mmol) was added thereto. The mixture was stirred at room temperature for 15 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (8:1, v/v) were collected, concentrated and recrystallized from diisopropyl ether-methanol to give the titled compound (225 mg, 53%) as white crystals.

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with ethyl acetate-methanol (8:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from diisopropyl ether-methanol

Sources & evidence

ORD record
ord-8d28232a5e1440938d38dbc5a00995ab
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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