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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
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HRID 43961 반응식
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]
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참가 물질

5

반응물 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

생성물 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-carboxamide수율 35%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b18051db88054fe8b74e20c029cd30a5
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08536197B2

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