Dimethyl Sulfoxide → (S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131435Notes

Reaction equation

[CH:1]1[C:10]2[C:9]([NH2:11])=[N:8][C:7]3[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=3[NH:5][C:4]=2[S:3][CH:2]=1.[CH3:16][O:17][CH2:18][CH2:19][C@H:20]1[CH2:25]N[CH2:23][CH2:22][NH:21]1.CS(C)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:16][O:17][CH2:18][CH2:19][C@@H:20]1[NH:21][CH2:22][CH2:23][N:11]([C:9]2[C:10]3[CH:1]=[CH:2][S:3][C:4]=3[NH:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[N:8]=2)[CH2:25]1

Participants

Conditions

Temperature: 105 °C

Procedure

Combine 4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (1.26 g, 5.85 mmol), (S)-2-(2-methoxy-ethyl)-piperazine (2.53 g, 17.56 mmol), DMSO (4.0 ml), and toluene (16.0 ml). Stir and heat the mixture at 105° C. After 24 hours, cool the mixture to ambient temperature. Dilute the mixture with ethyl acetate and wash the organic layer with 0.1N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (85:15) to give 395.8 mg (20%) of an brown foam: mass spectrum (ion spray): m/z=343.1 (M+1).

Workup

temperaturecool the mixture to ambient temperature
washwash the organic layer with 0.1N NaOH and brine
dry with materialDry (sodium sulfate)
concentrationconcentrate the organic layer to residue
customPurify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (85:15)

Sources & evidence

ORD record: ord-b52181b7392e495581fbbcede4880dd0
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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