(S)-2-Benzylpiperazine → (S)-2-Cyclopentyl-10-(3-benzyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 1350471Notes

Reaction equation

HRID 1350471 reaction equation
[CH2:1]([C@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]1([C:19]2[S:28][C:27]3[NH:26][C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[NH:23][C:22](=S)[C:21]=3[N:20]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[CH:14]1([C:19]2[S:28][C:27]3[NH:26][C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[N:23]=[C:22]([N:12]4[CH2:11][CH2:10][NH:9][C@@H:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:13]4)[C:21]=3[N:20]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 20760001(S)-2-BenzylpiperazineHCID 210934692-Cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione

Product 1

HCID 136005599(S)-2-Cyclopentyl-10-(3-benzyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using a method similar to the method of Example 491, using (S)-2-benzyl-piperazine (1.23 g, 7.0 mmol), 2-cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione (0.602 g, 2.0 mmol) in 8 ml of pyridine Obtain 240 mg light brown foam of title compound. Mass spectrum (electrospray) (m/e): C26H29N5S, Cacl. Mass: 443.36; Found: 444.1 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm: 7.32–7.21 (m, 5H), 7.03–6.97 (m, 2H), 6.86 (dt, 1H, J=7.8 Hz, J=1.9 Hz), 6.61 (d, 1H, J=7.8 Hz), 5.00 (br, 1H), 3.21–2.90 (m, 4H), 2.78–2.72 (m, 1H), 2.62–2.56 (m, 1H), 2.03–1.95 (m, 2H), 1.77–1.62 (m, 10H).

Sources & evidence

ORD record
ord-7efd6ffc152d4743be6060d971ffc840
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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