Hydrochloric Acid → cis(+/-)-2-[4-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-2-oxopyridin-1(2H)-yl]-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 1425204노트

반응식

HRID 1425204 반응식
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][N:21]([C:24]4[S:25][C:26]([C:30]([O:32]CC)=[O:31])=[C:27]([CH3:29])[N:28]=4)[C:20](=[O:35])[CH:19]=3)[CH2:14][C@H:13]2[O:36][CH2:37][CH3:38])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Na+].Cl>O1CCOCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][N:21]([C:24]4[S:25][C:26]([C:30]([OH:32])=[O:31])=[C:27]([CH3:29])[N:28]=4)[C:20](=[O:35])[CH:19]=3)[CH2:14][C@H:13]2[O:36][CH2:37][CH3:38])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86648677Ethyl cis(+/-)-2-[4-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-2-oxopyridin-1(2H)-yl]-4-methyl-1,3-thiazole-5-carboxylate

생성물 1

HCID 86648678cis(+/-)-2-[4-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-2-oxopyridin-1(2H)-yl]-4-methyl-1,3-thiazole-5-carboxylic acid수율 44%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

실험 절차

Ethyl cis(±)-2-[4-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-2-oxopyridin-1(2H)-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (140b) (10.8 mg, 0.0192 mmol) was dissolved in dioxane (0.5 mL). A 1 N aqueous sodium hydroxide solution (0.5 ml, 0.5 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction solution was neutralized with 1 N hydrochloric acid and brine was added, followed by extraction with chloroform three times. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Thereafter, the residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=9/1) to obtain 4.5 mg of the title compound as a colorless solid (44%).

후처리

  1. additionwas added
  2. extractionfollowed by extraction with chloroform three times
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThereafter, the residue was purified by silica gel column chromatography (elution solvent: dichloromethane/methanol=9/1)

출처 및 근거

ORD 기록
ord-4cb1b2067e834791a88042558bb5d400
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927588B2

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