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

HRID 131455ノート

反応式

HRID 131455 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][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

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 1363885767-Chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

生成物 1

HCID 135434004(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene収率 36.2%

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 (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).

後処理

  1. temperaturecool the mixture to ambient temperature
  2. stirringstir it for 16 hours
  3. washwash the organic layer with 0.1N NaOH and brine
  4. dry with materialDry (sodium sulfate)
  5. concentrationconcentrate the organic layer to residue
  6. 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-7d0f37f5ab52410993de3d9113428afc
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…