Potassium Phosphate, Tribasic → 1-(2-Chloropyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one

HRID 523528

反応式

HRID 523528 の反応式
CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:19]1([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[N:28]2[CH2:32][CH2:31][NH:30][C:29]2=[O:33])[CH2:21][CH2:20]1.[Cl:34][C:35]1[CH:40]=[C:39](I)[CH:38]=[CH:37][N:36]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[Cl:34][C:35]1[CH:40]=[C:39]([N:30]2[CH2:31][CH2:32][N:28]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][C:22]=3[CH:19]3[CH2:21][CH2:20]3)[C:29]2=[O:33])[CH:38]=[CH:37][N:36]=1

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 15165112-Chloro-4-iodopyridineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

生成物 1

HCID 665764121-(2-Chloropyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one収率 41%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

Copper iodide (6.5 mg, 0.034 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (4.8 mg, 0.034 mmol) and potassium phosphate (219.3 mg, 1.034 mmol) were added to a solution of 1,4-dioxane (5 mL) previously purged with nitrogen (10 minutes). The reaction mixture was purged with argon for 10 minutes, followed by the addition of 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 70 mg, 0.344 mmol) and 2-chloro-4-iodopyridine (99.09 mg, 0.413 mmol). The reaction mixture was heated to reflux at 120° C. overnight. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 42 mg of the product (41% yield).

後処理

  1. custompreviously purged with nitrogen (10 minutes)
  2. customThe reaction mixture was purged with argon for 10 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. concentrationThe organic layer was concentrated
  7. customto yield the crude product
  8. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

出典と根拠

ORDレコード
ord-f5e55f224cc042d09e56ecfca1061a20
出典データセット
uspto-grants-2016_05
特許番号
US09339501B2

関連ノート

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