2-Aminopyridine → [N-(2-Pyridyl)aminometyl](10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketone

HRID 1059420Notes

Reaction equation

HRID 1059420 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].Br[CH2:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]2[S:25][C:24]3[N:26]=[CH:27][CH:28]=[N:29][C:23]=3[N:22]([CH2:30][O:31][CH3:32])[C:21]=2[CH:33]=1)=[O:16]>C(O)C.O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]2[S:25][C:24]3[N:26]=[CH:27][CH:28]=[N:29][C:23]=3[N:22]([CH2:30][O:31][CH3:32])[C:21]=2[CH:33]=1)=[O:16]

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 18670316bromomethyl(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketone

Product 1

HCID 23565187[N-(2-Pyridyl)aminometyl](10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketoneYield 53.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3 ml of a solution of 140 mg of 2-aminopyridine in ethanol was added 130 mg of sodium hydrogencarbonate and the resulting mixture was stirred at room temperature. Next, 2 ml of a solution of 360 mg of bromomethyl(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)ketone in tetrahydrofuran was dropped thereinto and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was brought back to room temperature and silica gel was added thereto. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 200 mg of the title compound as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customwas brought back to room temperature
  4. additionsilica gel was added
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-b2931bce4ed943fbad0e1c2d558c95a9
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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