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

HRID 523528

반응식

HRID 523528 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 887Methanol용매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f5e55f224cc042d09e56ecfca1061a20
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339501B2

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