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

HRID 1454776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454776
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

Komponenten

9

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5b57cb4cb2cc4353bbd0230311c2715f
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482338B2

Notizen zur Reaktion

Wird geladen…