Hydrochloric Acid → n-{2-[n-(5-Chloro(2-pyridyl))carbamoyl]-4-methylphenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide

HRID 12155

Reaction equation

HRID 12155 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.Cl.[CH3:30][NH:31][CH2:32][CH2:33]N>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[N:31]([CH3:30])[CH2:32][CH2:33][N:28]=3)=[CH:25][CH:26]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8014N-MethylethylenediamineHCID 22596418n-{2-[n-(5-Chloro(2-pyridyl))carbamoyl]-4-methylphenyl}(4-cyanophenyl)carboxamide

Product 1

HCID 10160926n-{2-[n-(5-Chloro(2-pyridyl))carbamoyl]-4-methylphenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a lotion of the compound of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methylphenyl}(4-cyanophenyl)carboxamide (830 mg, 2.1 mmol) in anhydrous methanol (5 ml) and ethyl acetate (10 ml) was saturated with hydrogen chloride gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the residue was dissolved in anhydrous methanol (5 ml) and N-methylethylenediamine (0.926 ml, 10.5 mmol) was added. 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-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-methylphenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide as a white powder. MS found for C24H22ClN5O2 M+=448, (M+2)+=450.

Workup

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

Sources & evidence

ORD record
ord-fc958fa311974f6596f2ee991a7694ea
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Linked notes

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