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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(3-Iodo-4-methylphenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole

HRID 535815
Notes
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Reaction equation

HRID 535815 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[NH2:16])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1.[I:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:21](O)=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CC(O)=O>[I:17][C:18]1[CH:19]=[C:20]([C:21]2[NH:1][C:2]3[CH:3]=[C:4]([CH2:5][N:6]4[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]4)[CH:13]=[CH:14][C:15]=3[N:16]=2)[CH:24]=[CH:25][C:26]=1[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6216403-Iodo-4-methylbenzoic acidHCID 591273961-(3,4-Diaminobenzyl)-4-methylpiperazine

Product 1

HCID 867095552-(3-Iodo-4-methylphenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazoleYield 30.3%

Reagents, catalysts & solvents

2
HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3,4-diaminobenzyl)-4-methylpiperazine (10 mmol), 3-iodo-4-methylbenzoic acid (2.6 g, 10 mmol), EDCI (11 mmol), and HOBt (11 mmol) in dry DMF (25 mL) was stirred at ambient temperature for 24 hrs. The mixture was then evaporated in vacuo and the crude residue was dissolved in CH2Cl2 (100 mL) was washed with water (100 mL), brine (100 mL) and then dried by Na2SO4, filtered and concentrated. The residue obtained was dissolved in AcOH (30 mL) and heated at reflux for 3 hrs. The reaction mixture was evaporated in vacuo and the residue was purified by silica gel chromatography (eluent: 10% MeOH in CH2Cl2, MeOH was added 0.5% Et3N) to give a yellow solid (1.35 g, 30.3%). 1H NMR (300 MHz, CDCl3) δ: 8.50 (1H, s), 7.94-7.97 (1H, d, J=9.0 Hz), 7.53-7.56 (1H, d, J=9.0 Hz), 7.52-7.55 (1H, d, J=9.0 Hz), 7.30 (1H, s), 7.20-7.23 (1H, d, J=9.0 Hz), 3.60 (2H, s), 2.54 (8H, brs), 2.45 (3H, s), 2.32 (3H, s).

Workup

  1. customThe mixture was then evaporated in vacuo
  2. dissolutionthe crude residue was dissolved in CH2Cl2 (100 mL)
  3. washwas washed with water (100 mL), brine (100 mL)
  4. dry with materialdried by Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue obtained
  8. temperatureheated
  9. temperatureat reflux for 3 hrs
  10. customThe reaction mixture was evaporated in vacuo
  11. customthe residue was purified by silica gel chromatography (eluent: 10% MeOH in CH2Cl2, MeOH was added 0.5% Et3N)

Sources & evidence

ORD record
ord-c312fd58c50a4097a148fab0453c5c80
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859553B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes