Hydrochloric Acid → 6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl [4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide

HRID 12130

Reaction equation

HRID 12130 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)=[O:19])=[C:15]([O:28][CH3:29])[C:14]([O:30][CH3:31])=[C:13]([O:32][CH3:33])[CH:12]=2)=[O:10])=[N:6][CH:7]=1.Cl.[CH3:35][NH:36][CH2:37][CH2:38]N>CO.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:36]([CH3:35])[CH2:37][CH2:38][N:27]=4)=[CH:22][CH:21]=3)=[O:19])=[C:15]([O:28][CH3:29])[C:14]([O:30][CH3:31])=[C:13]([O:32][CH3:33])[CH:12]=2)=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8014N-MethylethylenediamineHCID 22596311N-{6-(N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide

Product 1

HCID 225963186-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl [4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamideYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of N-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide (680 mg, 1.33 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 (0.586 ml, 6.65 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-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide as a white powder (240 mg, 32%). MS found for C26H26BrN5O5 M+=568, (M+2)+=570.

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-7769d72acc204e3c94f7a4faf46f2404
Source dataset
uspto-grants-2010_06
Patent number
US07727982B2

Linked notes

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