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

HRID 131456

反応式

HRID 131456 の反応式
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][CH2:22][C@H:23]1[CH2:28]N[CH2:26][CH2:25][NH:24]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[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][CH2:20][O:19][CH3:18])[CH2:28]3)=[N:14][C:5]=2[CH:4]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 45099475(2S)-2-(3-Methoxypropyl)piperazineHCID 1363885767-Chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

生成物 1

HCID 136090412(S)-7-Chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene収率 26.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

Combine 7-chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (786.7 mg, 2.75 mmol), (S)-2-(3-methoxy-propyl)-piperazine (870.0 mg, 5.50 mmol), DMSO (2.0 ml), and toluene (8.0 ml). Stir and heat the mixture at 105° C. After 48 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 280.3 mg (26%) of the title compound: mass spectrum (ion spray): m/z=391.1 (M+1).

後処理

  1. temperaturecool the mixture to ambient temperature
  2. washwash the organic layer with 0.1N NaOH and brine
  3. dry with materialDry (sodium sulfate)
  4. concentrationconcentrate the organic layer to residue
  5. customPurify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10)

出典と根拠

ORDレコード
ord-7bd72c75277b47248d9caddc669b5009
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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