Pyrrolidine → HCID 178518322, compound

HRID 2236916Notes

Reaction equation

HRID 2236916 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[CH:12][NH:13][C:14]2[CH:25]=[CH:24][C:17]([CH2:18]OS(C)(=O)=O)=[CH:16][CH:15]=2)[C:4](=[O:26])[NH:3]1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[N:27]1([CH2:18][C:17]2[CH:24]=[CH:25][C:14]([NH:13][CH:12]=[C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[O:1])[NH:3][C:4]3=[O:26])=[CH:15][CH:16]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178505255HCID 178505255, compound

Product 1

HCID 178518322HCID 178518322, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of crude methanesulfonic acid 4-[(1,3-dioxo-2,3-dihydro-1H-isoquinolin-4-ylidenemethyl)-amino]-benzyl ester (72 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL) is added pyrrolidine (21 μL, 0.25 mmol). The reaction mixture is shaken at ambient temperature for 16 hours. The reaction mixture is diluted to 2 mL with N,N-dimethylformamide and purified by C18 reverse phase HPLC. The pure fractions were combined and concentrated to yield the title compound (3.0 mg).

Workup

  1. custompurified by C18 reverse phase HPLC
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3801b2e4b5b5461483c140077d4e29b5
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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