HCID 18704982, compound → HCID 178523915, compound

HRID 376331Notes

Reaction equation

HRID 376331 reaction equation
CS[C:3]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)=[N:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:25][C:26]1[CH:43]=[CH:42][C:29]([CH2:30][N:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH2:32][CH2:33][CH2:34][NH2:35])=[CH:28][CH:27]=1>N1C=CC=CC=1>[Br:25][C:26]1[CH:43]=[CH:42][C:29]([CH2:30][N:31]([CH2:32][CH2:33][CH2:34][NH:35][C:3]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]2)=[N:4][C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 18704982HCID 18704982, compoundHCID 22118499HCID 22118499, compound

Product 1

HCID 178523915HCID 178523915, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of N-[methylsulfanyl-(4-(pyridin-2-yl)piperazin-1-yl)methylene]-benzamide (2.9 g, 8.52 mmol) in pyridine (50 ml) was added N1-(4-bromobenzyl)-N1-(pyridin-2-yl)-propane-1,3-diamine (3 g, 9.37 mmol) and the reaction mixture was heated at reflux for 18 h. The volatiles were evaporated in vacuo and the residue dissolved in dichloromethane (100 ml) and evaporated in vacuo. The residue was purified by column chromatography on silica gel (600 ml) using first a mixture of ethyl acetate/triethylamine 95:5 (1 l) followed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents affording 2.95 g of N-[[3-[N-(4-bromo-benzyl)-N-(pyridin-2-yl)amino]propylamino]-(4-pyridin-2-yl-piperazin-1-yl) methylene]benzamide as a foam.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customThe volatiles were evaporated in vacuo
  4. dissolutionthe residue dissolved in dichloromethane (100 ml)
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (600 ml)
  7. additiona mixture of ethyl acetate/triethylamine 95:5 (1 l)
  8. additionfollowed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents

Sources & evidence

ORD record
ord-a4c7dcd9268a46e5b52a47034cb3f5fa
Source dataset
uspto-grants-2000_02
Patent number
US06020349

Reaction notes

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