Dimethylformamide → HCID 14390452, Verbindung

HRID 623137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623137
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([OH:21])=O)[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:22][N:23](C)C=O.S(Cl)(Cl)=O.CN>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([NH:23][CH3:22])=[O:21])[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 15097588HCID 15097588, Verbindung

Produkt 1

HCID 14390452HCID 14390452, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A slurry of 5-chloro-2-(4-methylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.8 g, 0.0093 mole) in tetrahydrofuran (11.3 ml) and dimethylformamide (0.68 g, 0.0093 mole) was cooled in an ice bath under nitrogen. Thionyl chloride (1.22 g, 0.0102 mole) was added dropwise to the stirred suspension. After stirring at room temperature for twenty minutes, the solution was cooled again in an ice bath and a solution of methylamine in tetrahydrofuran (21.5 ml of a 2.59M solution, 0.056 mole) was added dropwise. The suspension was stirred at room temperature under nitrogen for one hour and then the solvents were removed under reduced pressure. The residue was triturated in water (100 ml) and the resulting solid was collected by filtration and rinsed three times with water. The solid was dissolved in hot isopropyl alcohol, filtered while hot, and brought to the cloud point with isopropyl ether. Upon cooling, a solid precipitated which was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at 70° C. to give 1.86 g (64% yield) of title compound, mp>250° C.

Aufarbeitung

  1. temperaturethe solution was cooled again in an ice bath
  2. stirringThe suspension was stirred at room temperature under nitrogen for one hour
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated in water (100 ml)
  5. filtrationthe resulting solid was collected by filtration
  6. washrinsed three times with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. filtrationfiltered while hot, and
  9. temperatureUpon cooling
  10. customa solid precipitated which
  11. filtrationwas collected by filtration
  12. washrinsed with isopropyl ether
  13. customdried under high vacuum at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-e7e50bedc5e7481e8ca49d4521ce2ebb
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772600

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