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

HRID 1350469Notes

Reaction equation

HRID 1350469 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]1([C:13]2[S:22][C:21]3[NH:20][C:19]4[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=4[NH:17][C:16](=S)[C:15]=3[N:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1>N1C=CC=CC=1>[CH:8]1([C:13]2[S:22][C:21]3[NH:20][C:19]4[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=4[N:17]=[C:16]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)[C:15]=3[N:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 210934692-Cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione

Product 1

HCID 1357977312-Cyclopentyl-10-(4-methyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azuleneYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine N-methyl piperazine (0.264 g, 2.64 mmol) and 2-cyclopentyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo{f}azulene-10-thione (0.205 g, 0.66 mmol) in 7 ml of pyridine, and heat to reflux over night. 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 165 mg foam, which recrystallize in methanol to give 110 mg of title compound: Mass spectrum (electrospray) (m/e): C20H25N5S, Cacl. Mass (M): 367.18, Found: 368.18 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm: 6.97–6.90 (m, 2H), 6.81 (dt, 1H, J=7.3 Hz, J=1.0 Hz), 6.55 (dd, 1H, J=7.8 Hz, J=1.5 Hz), 4.96 (br, 1H), 3.2–3.17 (m, 1H), 2.49–2.47 (m, 4H), 2.28 (s, 3H), 2.03–1.97 (m, 2H), 1.71–1.55 (m, 10H).

Workup

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

Sources & evidence

ORD record
ord-b85cfbceb66143c6bec8377eb6810313
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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