Potassium Carbonate → O,O-Diethyl [6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylamidothiophosphate

HRID 499480Notes

Reaction equation

HRID 499480 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])=[S: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])=[S:28])[CH:11]=[CH:12][CH:13]=2)=[N:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750319O,O-Diethyl [6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methylamidothiophosphateYield 85.9%

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 chlorothiophosphate (410 mg, 2.2 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 2 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:2, v/v) were collected, concentrated and recrystallized from ethyl acetate-hexane to give the titled compound (362 mg, 82%) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-baa0475e9b694da2b7d16f2c5b464501
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…