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Pyridine → 5-{4-[6-(4-Acetylamino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

HRID 2303763
ノート
印刷プレビュー

反応式

HRID 2303763 の反応式
[ClH:1].Cl.[NH2:3][C:4]1[C:36]([CH3:37])=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][C:5]=1[CH3:38].[C:39](OC(=O)C)(=[O:41])[CH3:40].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.O1CCCC1>[ClH:1].[C:39]([NH:3][C:4]1[C:5]([CH3:38])=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[CH:21][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:31][CH:32]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:35][C:36]=1[CH3:37])(=[O:41])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 16719220Efatutazone Dihydrochloride

生成物 1

HCID 867584265-{4-[6-(4-Acetylamino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride収率 62%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

A mixture of 155 mg of 5-{4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione dihydrochloride, 36 mg of acetic anhydride, 107 mg of pyridine, 7.3 mg of 4-(N,N-dimethylamino)pyridine and 5 ml of anhydrous tetrahydrofuran was heated under reflux for 2 hours. The reaction mixture was concentrated by evaporation. Water was added to the concentrate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. To the residue, 10 ml of 4N hydrochloric acid/ethyl acetate were added, followed by stirring at room temperature for 21 hours. The insoluble product was collected by filtration, followed by washing with ether, whereby 97 mg of the title compound were obtained.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated by evaporation
  4. additionWater was added to the concentrate
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the residue, 10 ml of 4N hydrochloric acid/ethyl acetate were added
  9. filtrationThe insoluble product was collected by filtration
  10. washby washing with ether

出典と根拠

ORDレコード
ord-1461dec41dbf4128bbfe4768b288290d
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06432993B1

反応ノート

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