2-Pyridinemethanamine → N-[(2-pyridinyl)methyl]-1,3-dihydro-beta,beta-dimethyl-1,3-dioxo-2H-isoindole-2-propanamide

HRID 1294589Notes

Reaction equation

HRID 1294589 reaction equation
[CH3:1][C:2]([CH3:18])([N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])[CH2:3][C:4]([OH:6])=O.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>C(Cl)Cl>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][NH:19][C:4](=[O:6])[CH2:3][C:2]([CH3:1])([CH3:18])[N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 22038564beta,beta-Dimethyl-1,3dioxo-2-isoindolinepropionic acid

Product 1

HCID 69157702N-[(2-pyridinyl)methyl]-1,3-dihydro-beta,beta-dimethyl-1,3-dioxo-2H-isoindole-2-propanamideYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of β,β-dimethyl-1,3-dioxo-2-isoindolinepropionic acid (5 g, 20.2 mmol) and N,N-dicyclohexylcarbodiimide (4.6 g, 22.24 mmol) in 50 ml of dry methylene chloride is added 2-(aminomethyl)pyridine (2.41 g, 2.3 ml, 22.24 mmol) at ambient temperature. The mixture is stirred for 24 hours. The precipitate of dicyclohexyl urea is filtered off and discarded. The filtrate is evaporated and the residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 96:4) to give 3.97 g of N-[(2-pyridinyl)methyl]-1,3-dihydro-β,β-dimethyl-1,3-dioxo-2H-isoindole-2-propanamide (58%).

Workup

  1. filtrationThe precipitate of dicyclohexyl urea is filtered off
  2. customThe filtrate is evaporated
  3. customthe residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 96:4)

Sources & evidence

ORD record
ord-e1e85b7183114a8c9c08d60fa4ac7b93
Source dataset
uspto-grants-2007_07
Patent number
US07241772B2

Reaction notes

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