3,4-Diisopropoxy-3-cyclobutene-1,2-dione → HCID 22405688, Verbindung

HRID 441085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 441085
[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([NH2:27])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1.[CH3:28][CH:29]([O:31][C:32]1[C:33](=O)[C:34](=[O:40])[C:35]=1[O:36]C(C)C)[CH3:30]>C(O)C>[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:33]5[C:34](=[O:40])[C:35](=[O:36])[C:32]=5[O:31][CH:29]([CH3:30])[CH3:28])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 199620373-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-amino-1H-indole

Produkt 1

HCID 22405688HCID 22405688, VerbindungAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-aminoindole (6) (0.208 g, 0.56 mmol) and 3,4-bis (1-methylethoxy) cyclobut-3-ene-1,2-dione4 (2) (0.112 g, 0.56 mmol) in 5 mL of absolute ethanol was stirred at room temperature for 66 h and then it was heated at ca. 80° C. (oil-bath temperature) for 4 h. The cooled mixture was filtered and the residue was washed with ethanol and then dried in vacuo to give the title compound (0.190 g, 64%) as a slightly pinkish solid, mp 140°-143° C.: IR (KBr) 3312, 1800, 1720, 1607, 1588 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 10.80 (s, 1H), 10.7 (br s, 1H), 8.22 (s, 1H), 8.01 (s, 1H), 7.48 (m, 1H), 7.28 (d, J=8.6 Hz, 1H), 7.14 (s, 1H), 7.06 (m, 1H), 5.40 (m, 1H), 3.81 (s, 3H), 3.65 (br s, 4H), 3.42 (q, J=7.0 Hz, 0.6H, CH3CH2OH), 2.67 (m, 2H), 2.43 (m, 4H), 2.35 (m, 2H), 1.82 (m, 2H), 1.41 (d, J=6.1 Hz, 6H), 1.04 (t, J=7.0 Hz, 0.9H, CH3CH2OH). Anal. Calcd for C27H32N6O4. 0.5 H2O. 0.3 C2H6O: C, 62.85; H, 6.65; N, 15.94. Found: C, 62.85; H, 6.46; N, 16.17.

Aufarbeitung

  1. filtrationThe cooled mixture was filtered
  2. washthe residue was washed with ethanol
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a28dfc2a4d514298adc4b19874d20a7e
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521188

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