Acetic Acid → HCID 86626308, Verbindung

HRID 1097608

Reaktionsgleichung

Reaktionsgleichung von HRID 1097608
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][C:20]([NH:22][C:23](=NC(OC)=O)OC)=[O:21].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:16][C:14]([CH3:17])([CH3:15])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:23]1[NH:22][C:20](=[O:21])[O:19][CH3:18]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 14986941HCID 14986941, VerbindungHCID 853487891,3-dimethoxycarbonyl-O-methylisourea

Produkt 1

HCID 86626308HCID 86626308, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (1.0 g, 4.3 mmol), 1,3-dimethoxycarbonyl-O-methylisourea (prepared according to the general method of Viswanathan, N. Indian Patent No. 168,784, 1.64 g, 8.64 mmol), acetic acid (1.3 g, 22 mmol), and p-toluenesulfonic acid (0.82 g, 4.3 mmol) in methanol (20 mL) was heated at reflux for 16 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform (100 mL). The solution was washed sequentially with water (100 mL), aqueous sodium carbonate (100 mL of 4% w/w), water (100 mL), and brine (100 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform) followed by recrystallization from acetonitrile to provide 0.64 g of methyl [1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate as a white solid, mp 225° C.

Aufarbeitung

  1. customprepared
  2. temperatureat reflux for 16 hours
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform (100 mL)
  5. washThe solution was washed sequentially with water (100 mL), aqueous sodium carbonate (100 mL of 4% w/w), water (100 mL), and brine (100 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-472c74c0e8fe4f3da8c4ec9e479e1b28
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143270B2

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