2-Cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione → (S)-2-Cyclopentyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 1350470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350470
[CH2:1]([C@H:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:15]1([C:20]2[S:29][C:28]3[NH:27][C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[NH:24][C:23](=S)[C:22]=3[N:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1>N1C=CC=CC=1>[CH:15]1([C:20]2[S:29][C:28]3[NH:27][C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[N:24]=[C:23]([N:13]4[CH2:12][CH2:11][NH:10][C@@H:9]([CH2:1][CH2:2][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:14]4)[C:22]=3[N:21]=2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Komponenten

4

Edukt 2

HCID 210934692-Cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thioneHCID 44828673(S)-2-Phenethylpiperazine

Produkt 1

HCID 136005601(S)-2-Cyclopentyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azuleneAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Combine (S)-2-phenethyl-piperazine (0.537 g, 3.0 mmol) and 2-cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione (0.451 g, 1.5 mmol) in 10 ml of pyridine, and heat to 85° C. for 20 hour. Cool to room temperature, remove pyridine, the residue purify on silica gel using 2N ammonia in methanol/dichloromethane (1:10) as the eluent to give 265 mg of title compound as yellow solid. Mass spectrum (electrospray) (m/e): C27H31N5S, Cacl. Mass: 457.2; Found: 458.3 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm: 7.31–7.27 (m, 2H), 7.24–7.16 (m, 3H), 7.05–6.97 (m, 2H), 6.86 (dt, 1H, J=7.8 Hz, J=1.9 Hz), 6.62 (dd, 1H, J=7.8 Hz, J=1.0 Hz), 5.00 (br, 1H), 4.25 (br, 1H), 3.25 (t, 1H, J=7.8 Hz), 3.02–2.88 (m, 4H), 2.73–2.63 (m, 3H), 2.07–2.03 (m, 2H), 1.77–1.61 (m, 10H).

Aufarbeitung

  1. customremove pyridine
  2. customthe residue purify on silica gel using 2N ammonia in methanol/dichloromethane (1:10) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-d1983830f6c64a33baa6c63027bdb0a7
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214673B2

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