Methyl triflate → HCID 10317297, compound

HRID 131445Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:14][C:13](=S)[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1.FC(F)(F)S(OC)(=O)=O.[CH3:27][O:28][CH2:29][CH2:30][C@H:31]1[CH2:36][NH:35][CH2:34][CH2:33][NH:32]1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:35]3[CH2:34][CH2:33][NH:32][C@@H:31]([CH2:30][CH2:29][O:28][CH3:27])[CH2:36]3)[C:12]3[CH:11]=[C:10]([CH3:16])[S:9][C:8]=3[NH:7][C:6]=2[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Suspend 6-fluoro-2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione (500 mg, 1.9 mmol) in dichloromethane (30 ml), stir under nitrogen and cool in an ice/water bath. Add methyl trifluoromethanesulfonate (500 μl), and stir overnight. Concentrate the reaction mixture under reduced pressure, take up in pyridine (10 ml) and add (S)-2-(2-methoxyethyl)piperazine (400 mg, 2.78 mmol) and stir the reaction mixture under nitrogen and heat at 90° C. for three days. Concentrate the reaction mixture under reduced pressure and purify by flash column chromatography on silica gel (eluent dichloromethane/methanol) to give the desired as a yellow solid 727 mg: Mass Spectrum (FIA) 375 (M+1).

Workup

temperaturecool in an ice/water bath
concentrationConcentrate the reaction mixture under reduced pressure
stirringstir the reaction mixture under nitrogen
concentrationConcentrate the reaction mixture under reduced pressure
custompurify by flash column chromatography on silica gel (eluent dichloromethane/methanol)
customto give the

Sources & evidence

ORD record: ord-122d837db62946b7a7e276c4397ea1a1
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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