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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
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HRID 1479999 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 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
수율 58%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-b90ba1fb265845748dd4b03608ed3438
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409871B2

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