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

HRID 131441Notes

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][CH2:20][C@H:21]1[CH2:26]N[CH2:24][CH2:23][NH:22]1.CS(C)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:16][O:17][CH2:18][CH2:19][CH2:20][C@@H:21]1[NH:22][CH2:23][CH2:24][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)[CH2:26]1

Participants

Conditions

Temperature: 105 °C

Procedure

Combine 4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine (1.10 g, 5.11 mmol), (S)-2-(3-methoxy-propyl)-piperazine (1.62 g, 10.22 mmol), DMSO (4.0 ml), and toluene (16.0 ml). Stir and heat the mixture at 105° C. After 45 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 296.0 mg (16%) of the title compound: mass spectrum (ion spray): m/z=357.2 (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-3dee97c3d13b4db4b517d125a027bbf5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

Loading…