1-Methylpiperazine → HCID 86603557, compound

HRID 2111623Notes

Reaction equation

HRID 2111623 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]2[CH2:20][C:21]([OH:23])=O.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:5]2([CH:20]=[C:21]=[O:23])[N:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23084575HCID 23084575, compound

Product 1

HCID 86603557HCID 86603557, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,6-dimethyl-2-(3-fluorophenyl)-3-carboxymethyl-isoindolin-1-one [IUPAC name: 2-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid] (0.50 g, 1.6 mmol), 1-methylpiperazine (0.16 g, 1.6 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.31 g, 1.6 mmol) and 1-hydroxybenzotriazole hydrate (0.25 g, 1.6 mmol) were stirred in tetrahydrofuran (40 ml) at 25° C. for 16 hrs. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol=20:1) to give 0.56 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-d8596b7952794ac09ec320efd25a9054
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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