1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 7-Methyl-5-(4-methyl-piperazine-1-carbonyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427545Notes

Reaction equation

HRID 2427545 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]([OH:26])=O)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:24]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)=[O:26])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 53311336HCID 53311336, compound

Product 1

HCID 579497027-Methyl-5-(4-methyl-piperazine-1-carbonyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid (35 mg, 0.096 mmol), 1-methylpiperazine (12 μL, 0.11 mmol), EDCI (20 mg, 0.11 mmol), HOBT (14 mg, 0.11 mmol) were stirred in DMF (5 mL) for 18 hours at room temperature. The reaction mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated to yield 25 mg of a brown solid (70%). 1H NMR (300 MHz, CDCl3): δ 7.34-7.37 (m, 2H), 7.19-7.24 (m, 4H), 4.79 (s, 2H), 4.24 (s, 2H), 3.84 (br s, 2H), 3.44 (br s, 2H), 2.79 (s, 3H), 2.55 (br s, 2H), 2.36 (s, 5H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a05879d9322847efa3047b6f51079682
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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