Rosiglitazone → Rosiglitazone Maleate

HRID 2244603

反応式

HRID 2244603 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]>C(#N)C>[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 71%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
81 °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 stirred with 250 ml of dry acetonitrile and a suspension of maleic acid (19.50 gms, 0.168 mol) in 100 ml of dry acetonitrile was added at 27° C. to obtain a clear solution, followed by reflux for 30 minutes at 80-82° C. The reaction mass was gradually allowed to cool to 30° C. and stirred for 5 hours at 25-30° C. The precipitated solid was filtered under argon atmosphere and washed with 50 ml of dry acetonitrile. The filtered solid obtained was dried under vacuum at 30° C. for 5 hours, and at 50° C. for 6 hours, to obtain rosiglitazone maleate Form A (45 gms) in 71% yield.

後処理

  1. additionwas added at 27° C.
  2. customto obtain a clear solution
  3. temperatureto cool to 30° C.
  4. filtrationThe precipitated solid was filtered under argon atmosphere
  5. washwashed with 50 ml of dry acetonitrile
  6. customThe filtered solid obtained
  7. customwas dried under vacuum at 30° C. for 5 hours
  8. waitat 50° C. for 6 hours

出典と根拠

ORDレコード
ord-17854ad32bb441e78c96447742c24049
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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