3-Iodo-p-toluidine → N-(3-Iodo-4-methylphenyl)-4-((4methylpiperazin-1-yl) methyl)-3-(trifluoromethyl)benzamide

HRID 1527872Notes

Reaction equation

HRID 1527872 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:4][CH2:3]1.[I:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[CH3:30])[NH2:26].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(N(CC)CC)C.C(Cl)Cl>[I:22][C:23]1[CH:24]=[C:25]([NH:26][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][C:9]([CH2:8][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[CH:27]=[CH:28][C:29]=1[CH3:30]

Participants

7

Reactant 4

HCID 1188893-Iodo-p-toluidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 231458804-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 46838911N-(3-Iodo-4-methylphenyl)-4-((4methylpiperazin-1-yl) methyl)-3-(trifluoromethyl)benzamideYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a flask containing 1.0 g (2.67 mmol) of 4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)-benzoic acid (CAS#859027-02-4; prepared according to Asaki, T. et al. Bioorg. Med. Chem. Lett. (2006), 16, 1421-1425), 0.62 g (2.67 mmol) of 3-Iodo-4-methylaniline, 0.77 g (4.0 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC), and 0.43 g (3.2 mmol) of N-hydroxybenzotriazole monohydrate (HOBt.H2O) was added 5 mL of DCM and 5 mL of triethylamine. The solution was stirred at ambient temperature under an atmosphere of N2 for 3 days, concentrated, and the crude product purified by silica gel chromatography (eluted with 100% EtOAc then 10% MeOH/EtOAc), to provide 0.69 g of product as a white solid.

Workup

  1. concentrationconcentrated
  2. customthe crude product purified by silica gel chromatography (
  3. washeluted with 100% EtOAc

Sources & evidence

ORD record
ord-893c0a1d5fc14ebbacbc24971a3262c9
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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