1,4-Dioxane → Hydrochloric Acid

HRID 12773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12773
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:8](=[O:17])[NH:7][C:6]1=[O:18].[F:19][C:20]([F:34])([F:33])[C:21]1[CH:26]=[CH:25][C:24]([C@:27]23[CH2:32][C@H:31]2[CH2:30][NH:29][CH2:28]3)=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.O1CCOCC1>CCO>[ClH:1].[ClH:1].[ClH:1].[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[C:8](=[O:17])[NH:7][C:6](=[O:18])[N:5]([CH2:4][CH2:3][CH2:2][N:29]3[CH2:30][C@H:31]4[C@:27]([C:24]5[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:34])[F:33])=[CH:26][CH:25]=5)([CH2:32]4)[CH2:28]3)[CH:10]=2)[CH:12]=1

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 589941771-(3-Chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dioneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Produkt 2

HCID 313Hydrochloric AcidHCID 686928765-(3-pyridinyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-(3-chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dione (Prep43, 92 mg, 0.34 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 68 mg, 0.34 mmol), and DIPEA (134 μl, 1 mmol) in absolute EtOH (3 mL) was placed in a microwave oven and irradiated at 130° C. for 3 hours. The solvent was removed under vacuum and the residue was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The residue was purified by preparative LC-MS. After treatment with 4N HCl in dioxane (2 eq), the title compound was obtained (5 mg, 4% yield)

Aufarbeitung

  1. customirradiated at 130° C. for 3 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-64e8b09e11914286a0a842196707cf5b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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