Hydrochloric Acid → 1-[4-amino-2-ethoxymethyl-7-(1-methyl-1H-imidazol-2-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 598361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598361
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:24])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:32][C:33]1[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=1.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(N(CC)CC)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([OH:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:32][C:33]3[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=3)=[CH:5][C:4]=2[N:3]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 7365362-(chloromethyl)-1-methyl-1H-imidazoleHCID 1363405384-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Produkt 1

HCID 575452951-[4-amino-2-ethoxymethyl-7-(1-methyl-1H-imidazol-2-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-Amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (100 mg, 0.3 mmol), cesium carbonate (488 mg, 1.5 mmol), 2-chloromethyl-1-methyl-1H-imidazole.HCl (100 mg, 0.6 mmol), tetrabutylammonium bromide (96 mg, 0.3 mmol), triethylamine (0.5 ml), and DMF (10 mL) were combined and stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure and dichloromethane was added to the residue. Undissolved solids were removed by filtration. The filtrate was concentrated under reduced pressure and subsequently purified by flash column chromatography on silica gel, eluting with a gradient of 0-5% methanol in dichloromethane. The clean fractions were combined and concentrated under reduced pressure. The resulting solid was recrystallized from isopropanol/diethylether to yield 40 mg of 1-[4-amino-2-ethoxymethyl-7-(1-methyl-1H-imidazol-2-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off white solid, mp 200.0-202.0° C.

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure and dichloromethane
  2. additionwas added to the residue
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customsubsequently purified by flash column chromatography on silica gel
  6. washeluting with a gradient of 0-5% methanol in dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was recrystallized from isopropanol/diethylether

Quellen und Nachweise

ORD-Eintrag
ord-ea644f43a1834d909304c20bd815d92b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

Notizen zur Reaktion

Wird geladen…