2-Aminopyridine → HCID 57832788, Verbindung

HRID 729500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729500
NC1C=CC=CN=1.[I-].[NH2:9][N+:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>N1C=CC=CC=1>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]2[N:16]=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:28][CH:29]=1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 104392-AminopyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 129098391,2-Diaminopyridinium iodide2×

Produkt 1

HCID 57832788HCID 57832788, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2-Aminopyridine was converted to 1,2-diaminopyridinium iodide from a known literature method (J. Org. Chem., 31:260-265 (1996)). 1,2-Diaminopyridinium iodide (0.270 g, 1.1 mmol) was treated with 4-tert-butyl-benzoyl chloride (0.432 g, 2.2 mmol) in pyridine (2 mL). The reaction was heated at 85° C. in a sealed tube for 3 h, at which time the mixture was cooled to room temperature. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate extract was dried over magnesium sulfate and concentrated. The crude material was purified by flash silica gel chromatography, eluting with 25% ethyl acetate/hexanes (Rf=0.4) to yield 0.205 g (74%) of the purified product. MS (ES) m/z 252.2; HPLC (Method B): r.t.=6.7 min., purity 100% at 210-370 nm, 100% at 254 nm. HRMS: calcd for C16H17N3+H+, 252.14952; found (ESI, [M+H]30 ), 252.149.

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude material was purified by flash silica gel chromatography
  7. washeluting with 25% ethyl acetate/hexanes (Rf=0.4)

Quellen und Nachweise

ORD-Eintrag
ord-058ca0d1d56e4ff79cacecd226266326
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582636B2

Notizen zur Reaktion

Wird geladen…