2-(Pyridin-3-ylmethyl)isoindoline-1,3-dione → HCID 18670236, compound

HRID 1059358Notes

Reaction equation

HRID 1059358 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])[CH:21]=1>CN(C)C=O>[Cl-:1].[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][N+:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][N:27]4[C:31](=[O:32])[C:30]5=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]5[C:28]4=[O:37])[CH:21]=3)[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2

Participants

4

Reactant 2

HCID 7094552-(Pyridin-3-ylmethyl)isoindoline-1,3-dioneHCID 1133536310-methoxymethyl-8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 18670236HCID 18670236, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.587 g of 8-chloromethyl-10-(methoxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine and a solution of 0.524 g of N-(3-pyridylmethyl)phthalimide in 10 ml of dimethylforamide were heated to 80° C. in a nitrogen atmosphere for 4 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.489 g of the title compound as yellow crystals.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-532d94c36e8745d2821d228eae3f62a2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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