Acetic Acid → HCID 86626310, Verbindung

HRID 1097611

Reaktionsgleichung

Reaktionsgleichung von HRID 1097611
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[CH3:17][O:18][C:19]([NH:21][C:22](=NC(OC)=O)OC)=[O:20].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][CH:2]([CH3:16])[CH2:3][N:4]1[C:5]2[C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[C:22]1[NH:21][C:19](=[O:20])[O:18][CH3:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 53699038N4-Isobutyl-1,5-naphthyridine-3,4-diamineHCID 853487891,3-dimethoxycarbonyl-O-methylisourea

Produkt 1

HCID 86626310HCID 86626310, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine (Gerster et al, U.S. Pat. No. 6,194,425, Example 30 Part A, 4.10 g, 19.0 mmol), 1,3-dimethoxycarbonyl-O-methylisourea (7.21 g, 37.9 mmol), acetic acid (5.69 g, 94.8 mmol), and p-toluenesulfonic acid (3.60 g, 19.0 mmol) in methanol (50 mL) was heated at reflux for 16 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform (150 mL). The solution was washed sequentially with water (150 mL), aqueous sodium carbonate (150 mL of 4% w/w), water (150 mL), and brine (150 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 20% CMA in chloroform) followed by recrystallization from acetonitrile to provide 1.78 g of methyl [1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]carbamate as a white solid, mp 195-197° C.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (150 mL)
  4. washThe solution was washed sequentially with water (150 mL), aqueous sodium carbonate (150 mL of 4% w/w), water (150 mL), and brine (150 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 20% CMA in chloroform)
  7. customfollowed by recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-6678059f397a435994898fa220c42068
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143270B2

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