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

HRID 1531845

Reaction equation

HRID 1531845 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc07b0f986774c52b74867c3f8109621
Source dataset
uspto-grants-2001_03
Patent number
US06200986B1

Linked notes

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