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

HRID 598360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598360
[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]=[C:35]([C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)[S:36][CH:37]=1.C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)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]=[C:35]([C:38]4[S:39][CH:40]=[CH:41][CH:42]=4)[S:36][CH:37]=3)=[CH:5][C:4]=2[N:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 7364964-(Chloromethyl)-2-(thiophen-2-yl)-1,3-thiazoleHCID 1363405384-amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Produkt 1

HCID 575452861-[4-amino-2-ethoxymethyl-7-[2-(thiophen-2-yl)thiazol-4-ylmethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-olAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6342AcetonitrileLösungsmittel

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 (195 mg, 0.6 mmol), 4-(chloromethyl)-2-(2-thienyl)-1,3-thiazole (71 mg, 0.33 mmol), tetrabutylammonium bromide (10 mg, 0.03 mmol), triethylamine (0.5 ml), and acetonitrile (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 solid was recrystallized from acetonitrile to yield 82 mg of 1-[4-amino-2-ethoxymethyl-7-[2-(thiophen-2-yl)thiazol-4-ylmethoxy]-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off white powder, mp 192.0-194.0° 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 solid was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-7b56ca95d46d4e058de8a305fd6453e8
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

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