Picolinic acid → (1,4-Diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone

HRID 1454776Notes

Reaction equation

HRID 1454776 reaction equation
Cl.Cl.[N:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[NH:6][CH2:5][CH2:4]2.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](O)=[O:19].C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CO.C(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[N:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[N:6]([C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)=[O:19])[CH2:5][CH2:4]2

Participants

9

Reactant 5

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 173368391,4-Diazabicyclo[3.2.2]nonane dihydrochloride

Product 1

HCID 68865039(1,4-Diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a stirred solution of 1,4-diazabicyclo[3.2.2]nonane dihydrochloride (120 mg, 0.60 mmol), picolinic acid (85 mg, 0.69 mmol), and diisopropylethylamine (0.45 mL, 2.6 mmol) in dry DMF (2 mL) at ambient temperature was added in succession 1-hydroxybenzotriazole hydrate (85 mg, 0.63 mmol) and TBTU (200 mg, 0.62 mmol). The resulting precipitous mixture was stirred for 12 hours, partitioned between water and chloroform, and extracted with chloroform (3×). The organic layers were combined, washed with water, brine, and dried. The resulting product obtained from concentration of the organic phases was subjected to chromatography on silica gel eluting with a chloroform (ammoniated) to 15% MeOH/chloroform gradient to give (1,4-diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone. MS (ES+) 232 (MH+).

Workup

  1. custompartitioned between water and chloroform
  2. extractionextracted with chloroform (3×)
  3. washwashed with water, brine
  4. customdried
  5. customThe resulting product obtained from concentration of the organic phases

Sources & evidence

ORD record
ord-5b57cb4cb2cc4353bbd0230311c2715f
Source dataset
uspto-grants-2009_01
Patent number
US07482338B2

Reaction notes

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