Pyridine → (S)-10-[3-(3-Methoxy-propyl)-piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 131491Notes

Reaction equation

HRID 131491 reaction equation
[CH:1]([C:4]1[S:13][C:12]2[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7](=S)[C:6]=2[N:5]=1)([CH3:3])[CH3:2].O(C)S(C(F)(F)F)(=O)=O.[CH3:28][O:29][CH2:30][CH2:31][CH2:32][C@H:33]1[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1.N1C=CC=CC=1>ClCCl>[CH3:28][O:29][CH2:30][CH2:31][CH2:32][C@@H:33]1[NH:34][CH2:35][CH2:36][N:37]([C:7]2[C:6]3[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[S:13][C:12]=3[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]=2)[CH2:38]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9526Methyl triflateHCID 210934792-Isopropyl-4,9-dihydro-3-thia-1,4,9-triazabenzo[f]azulene-10-thioneHCID 45099475(2S)-2-(3-Methoxypropyl)piperazine

Product 1

HCID 135457471(S)-10-[3-(3-Methoxy-propyl)-piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 2-isopropyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo[f]azulene-10-thione (0.5 g, 1.816 mmol), methyl triflate (0.306 mL, 2.723 mmol) in dichloromethane (4 mL) and stir at ambient temperature for 2 hours. Evaporate the mixture uner reduced pressure and then combine the residue with (S)-2-(3-methoxy-propyl)-piperazine (0.287 g, 1.816 mmol) and pyridine (4 mL) and reflux for 8 hours. Concentrate the reaction mixture under reduced pressure and dilute the residue with ethyl acetata. Wash the organic with brine twice, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography, eluting with 2M ammonia in methanol:dichloromethane (5:95) to give the title compound: mass spectrum (m/e):400.03 (M+1).

Workup

  1. customEvaporate the mixture uner reduced pressure
  2. temperaturereflux for 8 hours
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. additiondilute the residue with ethyl acetata
  5. washWash the organic with brine twice
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customto give a residue
  10. customPurify the residue by flash chromatography
  11. washeluting with 2M ammonia in methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-683ab29264ea40749610aef2cfc523d7
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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