{4-[(2-Methylpyrrolidin-1-yl)methyl]phenyl}amine → HCID 178426157, compound

HRID 2236621Notes

Reaction equation

HRID 2236621 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/OC.[CH3:17][CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:19]2[CH2:20][CH2:21][CH2:22][CH:18]2[CH3:17])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 60974123{4-[(2-Methylpyrrolidin-1-yl)methyl]phenyl}amineHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178426157HCID 178426157, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.2 g (0.61 mmol) of (4E)-6-iodo-4-(methoxymethylene)-isoquinoline-1,3(2H,4H)-dione in 2 mL of N,N′-dimethylformamide is added {4-[(2-methylpyrrolidin-1-yl)methyl]phenyl}amine (0.14 mL, 0.73 mmol). The reaction mixture is heated at 100° C. under N2. Mass spectroscopy suggested the completion of reaction after 45 min. The reaction mixture is concentrated under high-pressure vacuum. Purification is performed by silica gel chromatography using 5% MeOH/CHCl3 as solvent. Concentrating the organic layer containing product afforded 0.043 g (14.5% yield) of yellow solid: mp 157-158° C.; MS (ESI) m/z 488.4 (M+H)+1

Workup

  1. customthe completion of reaction after 45 min
  2. concentrationThe reaction mixture is concentrated under high-pressure vacuum
  3. customPurification
  4. concentrationConcentrating the organic layer
  5. additioncontaining product

Sources & evidence

ORD record
ord-4869d284f09c42ee9f8ac2d582900d11
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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