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

HRID 131435ノート

反応式

HRID 131435 の反応式
[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

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 1363885834H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine

生成物 1

HCID 135457368(S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene収率 20%

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 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).

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 (85:15)

出典と根拠

ORDレコード
ord-b52181b7392e495581fbbcede4880dd0
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

読み込み中…