Pyridine → HCID 18670158, compound

HRID 1059397Notes

Reaction equation

HRID 1059397 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][NH:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:22]=[CH:23][CH:24]=[N:25][C:5]1=2.N1C=CC=CC=1.[CH2:32]([N:34]=[C:35]=[O:36])[CH3:33].[Cl-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:15]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[C:35]([NH:34][CH2:32][CH3:33])=[O:36])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:22]=[CH:23][CH:24]=[N:25][C:5]1=2

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 8022Ethyl isocyanateHCID 18670411HCID 18670411, compound

Product 1

HCID 18670158HCID 18670158, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

341 mg of 10-methoxymethyl-8-[N-(pyridin-3-yl)aminomethyl]-10H-pyrazino[2,3-b][1,4]benzothiazine was dissolved in 5 ml of toluene. After adding 3 ml of pyridine and 1.9 ml of ethyl isocyanate, the reaction mixture was heated under reflux for 3 days. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium chloride and extracted repeatedly with ethyl acetate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with toluene/acetone) to thereby give 350 mg of the title compound as a yellow oily substance.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3 days
  3. customAfter the completion of the reaction
  4. extractionextracted repeatedly with ethyl acetate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with toluene/acetone)

Sources & evidence

ORD record
ord-f6c476150a7e497e82f5de8095c720f6
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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