Sodium Carbonate → N-[3'-(Acetylamino)-1,1'-biphenyl-4-yl]-2-(1-azabicyclo[2.2.2]oct-3-yl)acetamide Hydrochloride

HRID 722187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722187
[C:1]([NH:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[ClH:20].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[CH:23]([CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=1)=[O:31])[CH2:22]2>CN(C=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]>[ClH:20].[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:36]2[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[CH2:29][CH:23]3[CH:24]4[CH2:25][CH2:26][N:21]([CH2:28][CH2:27]4)[CH2:22]3)=[CH:38][CH:37]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 218834482-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide Hydrochloride

Produkt 1

HCID 21883474N-[3'-(Acetylamino)-1,1'-biphenyl-4-yl]-2-(1-azabicyclo[2.2.2]oct-3-yl)acetamide Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

43.8 mg (0.24 mmol) of 3-(acetamido)phenylboronic acid, 0.33 ml (0.66 mmol) of 2M aqueous sodium carbonate solution and 8.1 mg (0.01 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride are added to a solution of 80 mg (0.22 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride in 1.5 ml of DMF. The reaction mixture is stirred at 80° C. for 0.14 h, cooled, filtered through kieselguhr and then purified by preparative HPLC. The product fractions are concentrated, taken up in methanol, mixed with 4M HCl in dioxane and again concentrated. Drying under high vacuum results in 23 mg (20% of theory) of the title compound.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered through kieselguhr
  3. custompurified by preparative HPLC
  4. concentrationThe product fractions are concentrated
  5. additionmixed with 4M HCl in dioxane
  6. concentrationagain concentrated
  7. customDrying under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a6f60b2052a14ef5a9001db55abf9616
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138410B2

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