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Hydrochloric Acid → 4-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-piperazine-1-carboxylic acid amide

HRID 416013
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HRID 416013 반응식
C([O:5][C:6](=O)[NH:7][CH:8]1C[CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[C:26]([Cl:28])[C:25]([CH2:29][CH:30]4[CH2:34][CH2:33][N:32]([CH:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)[C:31]4=[O:41])=[C:24]([Cl:42])[CH:23]=3)=[CH:18][CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.Cl.[O-]C#[N:47].[K+]>O1CCOCC1>[Cl:28][C:26]1[CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]([N:10]3[CH2:9][CH2:8][N:7]([C:6]([NH2:47])=[O:5])[CH2:12][CH2:11]3)=[O:15])=[CH:21][CH:20]=2)[CH:23]=[C:24]([Cl:42])[C:25]=1[CH2:29][CH:30]1[CH2:34][CH2:33][N:32]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:31]1=[O:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 66622263HCID 66622263, 화합물

생성물 1

HCID 577415454-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-piperazine-1-carboxylic acid amide수율 46.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

Dissolve racemic 4-[3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.40, 0.65 mmol) in dioxane (20 mL), add 4N hydrochloric acid in dioxane (10 mL) and stir 30 min to obtain an orange residue in reaction vessel. Concentrate under vacuum, dilute residue with water (10 mL) and add potassium cyanate (0.55 g, 0.68 mmol). Stir the reaction at room temperature to obtain a white precipitate. Filter off solid and wash with water. Dissolve the solid in dichloromethane and concentrate under vacuum to yield a clear foam. Use resin bound solid phase acidic media (SCX) to remove residual starting material and obtain 0.168 g (46%) of product as a white solid: MS (m/z): 557 (M+).

후처리

  1. customto obtain an orange residue
  2. customin reaction vessel
  3. concentrationConcentrate under vacuum, dilute residue with water (10 mL)
  4. stirringStir
  5. customthe reaction at room temperature
  6. customto obtain a white precipitate
  7. filtrationFilter off solid
  8. washwash with water
  9. dissolutionDissolve the solid in dichloromethane
  10. concentrationconcentrate under vacuum
  11. customto yield a clear foam
  12. customto remove residual

출처 및 근거

ORD 기록
ord-48fce9ea3d7a4813a0f9f73157894abc
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088776B2

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