Methyl triflate → (S)-10-[3-(2-Methoxyethyl)piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triazabenzo[f]azulene

HRID 131488Notes

Reaction equation

HRID 131488 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].COS(C(F)(F)F)(=O)=O.[CH3:28][O:29][CH2:30][CH2:31][C@H:32]1[CH2:37][NH:36][CH2:35][CH2:34][NH:33]1>ClCCl.N1C=CC=CC=1>[CH3:28][O:29][CH2:30][CH2:31][C@@H:32]1[NH:33][CH2:34][CH2:35][N:36]([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)[CH2:37]1

Participants

6

Reactant 3

HCID 9526Methyl triflateHCID 210934792-Isopropyl-4,9-dihydro-3-thia-1,4,9-triazabenzo[f]azulene-10-thioneHCID 55287560(S)-2-(2-Methoxyethyl)piperazine

Product 1

HCID 135485511(S)-10-[3-(2-Methoxyethyl)piperazin-1-yl]-2-isopropyl-4H-3-thia-1,4,9-triazabenzo[f]azuleneYield 58%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 2-isopropyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo[f]azulene-10-thione (2.61 g, 9.48 mmoles) with trifluoromethanesulfonic acid methyl ester (1.61 mL, 14.2 mmoles) in dichloromethane (20 mL). Stir at room temperature for 2 h, then remove solvent in vacuo. Suspend residue in pyridine (20 mL) and add (S)-2-(2-methoxyethyl)piperazine (1.37 g, 9.48 mmoles). Heat at 115° C. for 8 h, then remove solvent in vacuo and apply residue to silica gel column. Elute column with dichloromethane followed by 5% 2N ammonia-methanol in dichloromethane to obtain the title compound (2.11 g, 58%) as a yellow oil: mass spectrum (APCI): m/z=386.2 (M+1).

Workup

  1. temperatureHeat at 115° C. for 8 h
  2. washElute column with dichloromethane

Sources & evidence

ORD record
ord-413874f3bfb54f79a53fc8221d12fd4c
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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