Dimethyl Sulfoxide → (S)-6-Fluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131443Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([NH2:16])[C:13]3[CH:12]=[CH:11][S:10][C:9]=3[NH:8][C:7]=2[CH:17]=1.[CH3:18][O:19][CH2:20][CH2:21][C@H:22]1[CH2:27]N[CH2:25][CH2:24][NH:23]1.CS(C)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([N:16]3[CH2:25][CH2:24][NH:23][C@@H:22]([CH2:21][CH2:20][O:19][CH3:18])[CH2:27]3)[C:13]3[CH:12]=[CH:11][S:10][C:9]=3[NH:8][C:7]=2[CH:17]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Combine 6-fluoro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.20 g, 4.45 mmol), (S)-2(2-methoxy-ethyl)-piperazine (1.60 g, 11.12 mmol), DMSO (4.0 ml), and toluene (16.0 ml). Stir and heat the mixture at 105° C. After 40 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 (90:10) to give 400.4 mg (25%) of a tan foam: mass spectrum (ion spray): m/z 361.1 (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 (90:10)

Sources & evidence

ORD record: ord-f9c1869940eb4280b555054d3824acdb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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