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Triethylamine → 1-[4-amino-2-ethoxymethyl-7-(thiazol-4-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 598358
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598358
[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+].[CH:31]1[S:35][CH:34]=[N:33][C:32]=1[CH2:36]Cl.Cl.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)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][CH2:36][C:32]3[N:33]=[CH:34][S:35][CH:31]=3)=[CH:5][C:4]=2[N:3]=1
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 1363405384-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Produkt 1

HCID 575453141-[4-amino-2-ethoxymethyl-7-(thiazol-4-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
Ausbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

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), 4-(chloromethyl)thiazoleHCl (102 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 0-4% methanol in dichloromethane. The clean fractions were combined and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to yield 62 mg of 1-[4-amino-2-ethoxymethyl-7-(thiazol-4-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a white powder, mp 190.0-191.0° 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 0-4% methanol in dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c9990d687dfd489d8804312c99bb96af
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897597B2

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