Rosiglitazone → Rosiglitazone Maleate

HRID 2244602

反応式

HRID 2244602 の反応式
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>CO>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:23])=[CH:14][CH:13]=1.[CH:27](/[C:26]([OH:33])=[O:32])=[CH:28]/[C:29]([OH:31])=[O:30]

参加物

4

反応物 2

HCID 77999RosiglitazoneHCID 444266Maleic Acid

生成物 1

HCID 5281055Rosiglitazone Maleate収率 90%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
47.5 °C

実験手順

5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (rosiglitazone free base, 50 gms, 0.140 mol) was charged in 100 ml methanol and a solution of maleic acid (18.7 gms, 0.16 mol) in methanol (50 ml) was added under stirring and was further heated to 45-50° C. to obtain a clear solution. This solution was filtered (hot) through celite and ethyl acetate (500 ml) was added slowly to this clear filtrate under stirring at 25-30° C., and further stirred for 1 hour at 30° C., then chilled to 5-10° C. and stirred at the same temperature for 1 hour. The solid obtained was filtered under argon atmosphere and washed with 50 ml ethyl acetate. This solid was dried under vacuum at 50-55° C. to get rosiglitazone maleate Form A (60 gms) in 90% yield.

後処理

  1. customto obtain a clear solution
  2. filtrationThis solution was filtered (hot) through celite and ethyl acetate (500 ml)
  3. additionwas added slowly to this clear filtrate
  4. stirringunder stirring at 25-30° C.
  5. stirringfurther stirred for 1 hour at 30° C.
  6. temperaturechilled to 5-10° C.
  7. stirringstirred at the same temperature for 1 hour
  8. customThe solid obtained
  9. filtrationwas filtered under argon atmosphere
  10. washwashed with 50 ml ethyl acetate
  11. customThis solid was dried under vacuum at 50-55° C.

出典と根拠

ORDレコード
ord-8fca810debe7431c9692eceeae25077a
出典データセット
uspto-grants-2010_03
特許番号
US07678916B2

関連ノート

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