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 1425204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425204
[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]

Komponenten

6

Edukt 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

Produkt 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 acidAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4cb1b2067e834791a88042558bb5d400
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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