Water → 2-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

HRID 639481

Reaktionsgleichung

Reaktionsgleichung von HRID 639481
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:16]=[C:15]2[N:10]([C:11]([NH2:20])=[N:12][C:13]3[NH:19][CH:18]=[CH:17][C:14]=32)[N:9]=1.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH3:37])[CH2:26][CH2:25]1.O>CN(C=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[N:16]=[C:15]2[N:10]([C:11]([NH2:20])=[N:12][C:13]3[N:19]([CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][N:27]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[O:36][CH3:37])[CH2:28][CH2:29]4)[CH:18]=[CH:17][C:14]=32)[N:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineHCID 1363878362-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Produkt 1

HCID 250206692-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of NaH (13 mg, 0.32 mmol) in anhydrous DMF (2 mL) at 0° C. is added slowly a solution of the title B compound, 2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine (60 mg, 0.25 mmol) in 2 mL of anhydrous DMF. After stirring at 0° C. under N2 for 15 min, 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine (0.275 mmol) is added at 0° C. The mixture is warmed to RT and stirred overnight. The reaction mixture is then poured into water and extracted with DCM (3×). The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash chromatography using DCM/MeOH/NH4OH (98/2/0 2) as eluent to give 2-(furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine: LC/MS (M+1=459.2). 1H NMR (DMSO-d6, 400 MHz) δ 2.56 (m, 4H), 2.67 (t, 2H, J=6.0 Hz), 2.94 (m, 4H), 3.76 (s, 3H), 4.28 (t, 2H, J=6.0 Hz), 6.60 (d, 1H, J=3.2 Hz), 6.71 (m, 1H), 6.85 (m, 2H), 6.92 (m, 2H), 7.18 (m, 2H), 7.49 (brs, NH2), 7.91 (d, 1H, J=1.6 Hz).

Aufarbeitung

  1. temperatureThe mixture is warmed to RT
  2. stirringstirred overnight
  3. extractionextracted with DCM (3×)
  4. dry with materialThe organic layer is dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-478ef6fb892d4aa48f8cfd605c4827a6
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691869B2

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