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Dichloromethane → (6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-phenyl)-methanone

HRID 1766725
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1766725
C(OC(=O)[NH:7][CH:8]1[CH:13]2[CH:9]1[CH2:10][N:11]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1)[CH2:12]2)(C)(C)C.[Cl:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[C:27]([Cl:32])[C:26]=1[CH:33]([O:35][C:36]1[C:37]([NH2:51])=[N:38][CH:39]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:41]=1)[CH3:34].C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+].Cl.O1CCOCC1>COCCOC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:7][CH:8]1[CH:9]2[CH:13]1[CH2:12][N:11]([C:14]([C:15]1[CH:16]=[CH:17][C:18]([C:40]3[CH:39]=[N:38][C:37]([NH2:51])=[C:36]([O:35][CH:33]([C:26]4[C:27]([Cl:32])=[CH:28][CH:29]=[C:30]([F:31])[C:25]=4[Cl:24])[CH3:34])[CH:41]=3)=[CH:19][CH:20]=1)=[O:22])[CH2:10]2
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Komponenten

9

Edukt 5

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 204431481,4-Dioxane hydrochlorideHCID 211113943-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 58886163[3-(4-Iodo-benzoyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 21111335
(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-phenyl)-methanone
Ausbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of [3-(4-iodo-benzoyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-carbamic acid tert-butyl ester (100 mg, 0.234 mmol) and 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (100 mg, 0.234 mmol) in DME (2 mL) was added Pd(dppf)2Cl2.CH2Cl2 (10 mg, 0.012 mmol) and Cs2CO3 (351 mg, 0.702 mmol). The mixture was bubbled with nitrogen for 10 min then microwaved at 150° C. for 30 min. LCMS checked that the reaction was completed. The crude reaction mixture was diluted with ethyl acetate followed by washings with water and brine. The solution was dried over MgSO4. Purification by prep-HPLC afforded a solid. The solid was stirred with 4 N HCl/dioxane (3 mL) for 3 hr at room temperature. Removal of the volatiles led to a residue that was purified by prep-HPLC to afford (6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-(4-{6-amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-phenyl)-methanone (30 mg, yield 26%).

Aufarbeitung

  1. customThe mixture was bubbled with nitrogen for 10 min
  2. customthen microwaved at 150° C. for 30 min
  3. customThe crude reaction mixture
  4. washfollowed by washings with water and brine
  5. dry with materialThe solution was dried over MgSO4
  6. customPurification
  7. customby prep-HPLC afforded a solid
  8. customRemoval of the volatiles
  9. customwas purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-236016c546cc486ca0228cd88ff4625a
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07230098B2

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