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

HRID 558086ノート

反応式

HRID 558086 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de95a5a6e0db42ce8020fc50ea31d41a
出典データセット
uspto-grants-2011_11
特許番号
US08063036B2

反応ノート

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