Pyridine → (S)-2-Cyclopentyl-10-{3-[2-(3-methoxy-phenyl)-ethyl]-piperazin-1-yl}-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 1350472Notes

Reaction equation

HRID 1350472 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=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=[CH:37][CH:36]=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]([CH2:5][CH2:6][C:7]5[CH:37]=[CH:36][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=5)[CH2:14]4)[C:22]=3[N:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 1519333(S)-2-(3-methoxyphenyl)-piperazineHCID 210934692-Cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione

Product 1

HCID 136005570(S)-2-Cyclopentyl-10-{3-[2-(3-methoxy-phenyl)-ethyl]-piperazin-1-yl}-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Conditions

Temperature
85 °C

Procedure

By using a method similar to the method of Example 491, using (S)-2-(3-methoxy-phenyl)-piperazine (1.10 g, 5.0 mmol) and 2-cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione (0.540 g, 1.79 mmol) in 6 ml of pyridine, and heat to 85° C. for 5 hour. After purification, give 310 mg of title compound as brown solid. Mass spectrum (electrospray) (m/e): C28H33N5OS, Cacl. Mass: 487.24; Found: 488.1 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm: 7.21–7.17 (m, 1H), 7.05–6.97 (m, 2H), 6.86 (dt, 1H, J=7.3 Hz, J=1.9 Hz), 6.79–6.72 (m, 3H), 6.61 (dd, 1H, J=7.8 Hz, J=1.5 Hz), 5.00 (br, 1H), 4.25 (br, 1H), 3.78 (s, 3H), 3.02–2.89 (m, 4H), 2.69–2.63 (m, 3H), 2.07–2.04 (m, 2H1), 1.77–1.48 (m, 10M).

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-494d3e31188346e4bc79c0173ca9ecbb
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…