Water → 1-isobutyl-2-[(methoxyamino)methyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 2426368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426368
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]=[C:8]([NH2:14])[C:7]=2[N:15]=1.Cl.[O:21]([NH2:23])[CH3:22].C(N(CC)CC)C.O>CN(C=O)C>[CH2:16]([N:5]1[C:6]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]=[C:8]([NH2:14])[C:7]=2[N:15]=[C:4]1[CH2:3][NH:23][O:21][CH3:22])[CH:17]([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67262971HCID 67262971, Verbindung

Produkt 1

HCID 119562431-isobutyl-2-[(methoxyamino)methyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-(chloromethyl)-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (1.53 g, 5.05 mmol) was dissolved in 10 mL of DMF in a pressure tube under a nitrogen atmosphere. Methoxylamine hydrochloride (1.27 g, 15.15 mmol) and triethylamine (4.22 mL, 30.3 mmol) were added, the tube was sealed and the contents heated to 50° C. for two hours, then to 60° C. for five hours. The mixture was then stored in the refrigerator over the weekend. The contents were poured into water (60 mL) and stirred for 20 minutes. The solution was extracted with chloroform (3×70 mL) and the organics were washed with water (4×40 mL) and brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by HPFC eluting with a gradient of 0-30% CMA (80/18/2 v/v/v chloroform/methanol/concentrated ammonium hydroxide) in chloroform and then recrystallized from acetonitrile to provide 1-isobutyl-2-[(methoxyamino)methyl]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 154.0-156.0° C.

Aufarbeitung

  1. customthe tube was sealed
  2. extractionThe solution was extracted with chloroform (3×70 mL)
  3. washthe organics were washed with water (4×40 mL) and brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by HPFC
  8. washeluting with a gradient of 0-30% CMA (80/18/2 v/v/v chloroform/methanol/concentrated ammonium hydroxide) in chloroform
  9. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-3b89c2bcd62642aabca75b7d487bce7c
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968563B2

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