3,4-Diaminopyridine → 2-(2,3-Difluoro-phenyl)-1H-imidazo[4,5-c]pyridine

HRID 1992530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992530
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[NH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[NH2:22].[F:23][C:24]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](O)=O.[OH-].[Na+]>CS(O)(=O)=O>[F:23][C:24]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]1[NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[N:22]=1

Komponenten

6

Edukt 4

HCID 59183,4-DiaminopyridineHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 3705902,3-Difluorobenzoic acid

Produkt 1

HCID 272821652-(2,3-Difluoro-phenyl)-1H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

Phosphorous pentoxide (24.56 g) was dissolved in methanesulfonic acid (165.8 mL) at 50° C. with stirring. To the solution, 3,4-diaminopyridine (12.3 g, 0—11 moles) and 2,3-difluorobenzoic acid (19.4 g, 0.12 moles) were added. The reaction mixture was heated to 190° C. for 3 hours. The reaction was done three times. The reaction mixtures was cooled to 50° C. and poured into ice with stirring. At this stage, all three batches were combined. The reaction mixture was neutralized by the addition of NaOH with stirring until the pH is 8. Solid material precipitated out of solution, was collected by filtration and air-dried. The final product was re-crystallized from ethanol/water twice to yield 36 g of 2-(2,3-difluorophenyl)-3H-imidazo[4,5-c]pyridine. 1H 300 Mhz (CD3OD) sigma 7.3-7.42 (m, 1p); 7.43-7.58 (m, 1p); 7.70 (d, 1p); 8.0 (m, 1p); 8.34 (d, 1p); and 8.95 (s, 1p). LC/MS data M/z=232.

Aufarbeitung

  1. customThe reaction mixtures
  2. temperaturewas cooled to 50° C.
  3. additionpoured into ice
  4. stirringwith stirring
  5. stirringwith stirring until the pH is 8
  6. customSolid material precipitated out of solution
  7. filtrationwas collected by filtration
  8. customair-dried
  9. customThe final product was re-crystallized from ethanol/water twice

Quellen und Nachweise

ORD-Eintrag
ord-133a58efd9a64f3f8104a4b39474ae41
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648998B2

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