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Hydrochloric Acid → cis(+/-)-4-Chloro-N-[3-ethoxy-1-(5-methyl-6-oxo-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazol-2-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamide

HRID 43961
ノート
印刷プレビュー

反応式

HRID 43961 の反応式
C[Al](C)C.[Cl:5][C:6]1[N:7]=[C:8]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([C:22]3[S:23][C:24]([C:30]([O:32]CC)=O)=[C:25]([CH2:27][NH:28][CH3:29])[N:26]=3)[CH2:18][C@H:17]2[O:35][CH2:36][CH3:37])=[O:14])[NH:9][C:10]=1[CH2:11][CH3:12].Cl>C1(C)C=CC=CC=1>[Cl:5][C:6]1[N:7]=[C:8]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([C:22]3[S:23][C:24]4[C:30](=[O:32])[N:28]([CH3:29])[CH2:27][C:25]=4[N:26]=3)[CH2:18][C@H:17]2[O:35][CH2:36][CH3:37])=[O:14])[NH:9][C:10]=1[CH2:11][CH3:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 16682925TrimethylaluminumHCID 86648842Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(methylamino)methyl]-1,3-thiazole-5-carboxylate

生成物 1

HCID 86648843cis(+/-)-4-Chloro-N-[3-ethoxy-1-(5-methyl-6-oxo-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazol-2-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamide収率 35%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Trimethylaluminum (1.05 M solution in hexane) (0.76 mL, 0.80 mmol) was added to a solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(methylamino)methyl]-1,3-thiazole-5-carboxylate obtained in Example (256a) (80 mg, 0.16 mmol) in toluene (3 mL), and the mixture was heated under reflux for 45 minutes. A 1 N aqueous hydrochloric acid solution was added to the reaction solution, followed by stirring. Then, the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=20/1) to obtain 25 mg of the title compound as a pale yellow solid (35%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. extractionThen, the mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=20/1)

出典と根拠

ORDレコード
ord-b18051db88054fe8b74e20c029cd30a5
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536197B2

反応ノート

読み込み中…

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