Hydrochloric Acid → (S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 1609479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609479
Cl.Cl.[CH3:3][C:4]1[CH:5]=[C:6]([CH2:13][N:14]2[C:22]3[CH2:21][C@@H:20]([C:23]([OH:25])=[O:24])[NH:19][CH2:18][C:17]=3[N:16]=[CH:15]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl.[CH3:27]O>COC(OC)OC>[CH3:27][O:24][C:23]([C@H:20]1[NH:19][CH2:18][C:17]2[N:16]=[CH:15][N:14]([CH2:13][C:6]3[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH3:3])[CH:5]=3)[C:22]=2[CH2:21]1)=[O:25]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70345643(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride

Produkt 1

HCID 14457531(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl esterAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9005Trimethyl orthoformateLösungsmittel

Versuchsvorschrift

(S)-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride (VII-2) (1.1538g, 0.00296 mol) was suspended in dry methanol (46 ml) and trimethylorthoformate (4.6 ml). Hydrogen chloride was blown into the suspension to saturation under ice cooling and stirring. The reaction solution was then stirred on a 90° C. oil bath for 6 hours, cooled, and concentrated. The resulting yellowish brown oily material (0.7456 g) was purified by silica gel column chromatography (Kiesegel 60, 60 g, chloroform/methanol= 15/1) to obtain the objective compound (VI-2) (0.7076 g; yield: 72.3%) as an orange oily material.

Aufarbeitung

  1. stirringThe reaction solution was then stirred on a 90° C. oil bath for 6 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe resulting yellowish brown oily material (0.7456 g) was purified by silica gel column chromatography (Kiesegel 60, 60 g, chloroform/methanol= 15/1)
  5. customto obtain the objective compound (VI-2) (0.7076 g; yield: 72.3%) as an orange oily material

Quellen und Nachweise

ORD-Eintrag
ord-2a890baf6db44087adb63b22e3b17308
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05401736

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