Dimethyl Sulfoxide → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131455Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

Combine 7-Chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.20 g, 4.19 mmol), (S)-2-(2-methoxy-ethyl)-piperazine (1.51 g, 10.48 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 and stir it for 16 hours. 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 571.5 mg (36%) of an brown solid: mass spectrum (ion spray): m/z=377.1 (M+1).

Workup

temperaturecool the mixture to ambient temperature
stirringstir it for 16 hours
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-7d0f37f5ab52410993de3d9113428afc
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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