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Hydrochloric Acid → 1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl)-2-hydroxy-ethanone

HRID 1479999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1479999
[OH-].[K+].[CH2:3]([C:10]1[N:15]=[N:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[N:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][N:23]=3)[C@H:18]([CH3:31])[CH2:17]2)=[C:12]([CH3:32])[C:11]=1[CH3:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=[O:36])C.C(O)(=O)C.IC1C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>CO.O>[CH2:3]([C:10]1[N:15]=[N:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[N:26][C:25]([C:28](=[O:30])[CH2:29][OH:36])=[CH:24][N:23]=3)[C@H:18]([CH3:31])[CH2:17]2)=[C:12]([CH3:32])[C:11]=1[CH3:33])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
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Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 12217721Iodo benzene diacetateHCID 451071751-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-ethanone

Produkt 1

HCID 59191535
1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl)-2-hydroxy-ethanone
Ausbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of KOH (224 mg, 4.0 mmol) and CH3OH (10 mL) is added 1-[(R)-4-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl)-ethanone (400 mg, 1.0 mmol) in CH3OH (10 mL) and then iodobenzene diacetate (464 mg, 1.5 mmole) in portions at 0° C. The mixture is stirred at room temperature overnight. The solvent is removed and then extracted with DCM. The organic layer is washed with aqueous NH4Cl and afterwards concentrated to yield crude example 112. This material is dissolved in water and then 6 N HCl (5 mL) is added. The mixture is stirred at room temperature for 3 h. Afterwards it is made basic with NaHCO3 and extracted with DCM. The organic layer is concentrated to give a crude product that is purified by chromatography on silica gel (EtOAc/Heptane: 50%˜100%) to give the title compound (240 mg, 58%) as a yellow solid.

Aufarbeitung

  1. customat 0° C
  2. customThe solvent is removed
  3. extractionextracted with DCM
  4. washThe organic layer is washed with aqueous NH4Cl
  5. concentrationafterwards concentrated
  6. customto yield crude example 112
  7. stirringThe mixture is stirred at room temperature for 3 h
  8. extractionextracted with DCM
  9. concentrationThe organic layer is concentrated
  10. customto give a crude product that
  11. customis purified by chromatography on silica gel (EtOAc/Heptane: 50%˜100%)

Quellen und Nachweise

ORD-Eintrag
ord-b90ba1fb265845748dd4b03608ed3438
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409871B2

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