Hydrogen Sulfide → 5-chloro-N-(5-chloropyridin-2-yl)-2-(4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)benzamido)benzamide

HRID 1896714Notes

Reaction equation

HRID 1896714 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)=[O:10])=[C:4]([C:19](=[O:28])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)[CH:3]=1.S.IC.[CH3:32][NH:33][CH2:34][CH2:35]N>N1C=CC=CC=1.C(N(CC)CC)C.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[N:33]([CH3:32])[CH2:34][CH2:35][N:18]=3)=[CH:15][CH:16]=2)=[O:10])=[C:4]([C:19](=[O:28])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)[CH:3]=1

Participants

9

Reactant 4

HCID 402Hydrogen SulfideHCID 6328Methyl iodideHCID 8014N-MethylethylenediamineHCID 22596340n-{4-Chloro-2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide

Product 1

HCID 101621455-chloro-N-(5-chloropyridin-2-yl)-2-(4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)benzamido)benzamide

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound of N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (683 mg, 1.66 mmol) in anhydrous pyridine (10 ml) and triethyl amine (1 ml) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the residue was dissolved in anhydrous acetone (5 ml) and iodomethane (1 ml, 16.6 mmol) was added. The mixture was stirred under reflux condition for 2 hrs. After the evaporation of solvent, the residue was dissolved in anhydrous methanol (5 ml) and added a solution of N-methylethylenediamine (0.732 ml, 8.3 mmol) and acetic acid (1.5 ml) in anhydrous methanol (5 ml). The mixture was stirred under reflux condition for 2 hrs. After the evaporation of solvent, the crude residue was purified by RP-HPLC to give N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide as a white powder. MS found for C23H19Cl2N5O2 M+=468 (M+2)+=470.

Workup

  1. customAfter the evaporated the solvent
  2. dissolutionthe residue was dissolved in anhydrous acetone (5 ml)
  3. stirringThe mixture was stirred
  4. temperatureunder reflux condition for 2 hrs
  5. customAfter the evaporation of solvent
  6. dissolutionthe residue was dissolved in anhydrous methanol (5 ml)
  7. stirringThe mixture was stirred
  8. temperatureunder reflux condition for 2 hrs
  9. customAfter the evaporation of solvent
  10. customthe crude residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-20c9c668a01d467792007957ec6f0f6c
Source dataset
uspto-grants-2013_08
Patent number
US08518977B2

Reaction notes

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