Picolinic acid → N,N'-Bis(picolinovl)-2.5-diazabicyclo[2 .2.2]octane

HRID 1531845

Reaktionsgleichung

Reaktionsgleichung von HRID 1531845
[CH:1]12[CH2:8][CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][NH:2]2.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([OH:17])=O.CN([P+](O[N:29]1N=N[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C1C=C2N=NN([OH:54])C2=CC=1.O.CCN(C(C)C)C(C)C>CN(C=O)C.[Cl-].[Na+].O>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=1[C:35]([N:2]1[CH2:3][CH:4]2[CH2:7][CH2:8][CH:1]1[CH2:6][N:5]2[C:15](=[O:17])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1)=[O:54]

Komponenten

8

Edukt 5

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4233472,5-Diazabicyclo(2.2.2)octaneHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 9905241N,N'-Bis(picolinovl)-2.5-diazabicyclo[2 .2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Combine 2,5-diazabicyclo[2.2.2]octane (1 molar equivalent), picolinic acid (3 molar equivalents), BOP reagent (3 molar equivalents), HOBt hydrate (3 molar equivalents) and iPr2NEt (5 molar eqiuvalents) in DMF. Maintain the reaction at room temperature for 18 h. Quench the reaction by pouring into brine and extracting with EtOAc. Dry the combined organic extracts over Na2SO4 and remove the solvent in vacuo. Purification by flash chromatography gives the title product.

Aufarbeitung

  1. temperatureMaintain
  2. customthe reaction at room temperature for 18 h
  3. customQuench
  4. customthe reaction
  5. extractionextracting with EtOAc
  6. dry with materialDry the combined organic extracts over Na2SO4
  7. customremove the solvent in vacuo
  8. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc07b0f986774c52b74867c3f8109621
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200986B1

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