Ethanol → 2-(Ethoxymethyl)-1-[2-methyl-2-[2-(3-trityloxypropylamino)ethoxy]propyl]-imidazo[4,5-c]quinolin-4-amine

HRID 522829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522829
[NH2:1][CH2:2][CH2:3][O:4][C:5]([CH3:26])([CH3:25])[CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][O:22][CH2:23][CH3:24].[C:27]1([C:33]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:34][CH2:35][CH2:36][CH:37]=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)C.[BH4-].[Na+]>C(OCC)(=O)C.O>[CH2:23]([O:22][CH2:21][C:8]1[N:7]([CH2:6][C:5]([CH3:25])([O:4][CH2:3][CH2:2][NH:1][CH2:37][CH2:36][CH2:35][O:34][C:33]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:26])[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=1)[CH3:24]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 5712233-TrityloxypropanalHCID 4311764Sodium borohydrideHCID 1184515851-(2-(2-Aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 1184516062-(Ethoxymethyl)-1-[2-methyl-2-[2-(3-trityloxypropylamino)ethoxy]propyl]-imidazo[4,5-c]quinolin-4-amineAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(2-(2-Aminoethoxy)-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (50 mg, 140 μmol) and 3-(triphenylmethoxy)-propanal (CAN 67057-68-5; 44.3 mg, 140 μmol) were combined with ethanol (500 μL) to give a light yellow suspension. The mixture was stirred for 2 hours at room temperature. Afterwards sodium borohydride (5.82 mg, 154 μmol) was added and stirring at room temperature continued overnight. The mixture was stirred with water (2 mL) and ethyl acetate (5 mL), dried by passage through a ChemElut® cartridge and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane) followed by another flash chromatography (silica gel, 0 to 10% methanol in ethyl acetate) to give the title compound (10 mg, 11%) as yellowish gum; LC-MS (UV peak area, ESI) 89%, 658.5 (MH+).

Aufarbeitung

  1. customto give a light yellow suspension
  2. stirringstirring at room temperature
  3. waitcontinued overnight
  4. customdried by passage through a ChemElut® cartridge
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a1a65c679e0e4d49bc655999f6c987cb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334268B2

Notizen zur Reaktion

Wird geladen…