O-Methylhydroxylamine hydrochloride → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(methoxyimino)methyl-1,3-thiazole-5-carboxylate

HRID 1424970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424970
[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[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH:23]=O)[N:22]=3)[CH2:14][C@H:13]2[O:30][CH3:31])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.[CH3:33][O:34][NH2:35]>N1C=CC=CC=1>[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[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH:23]=[N:35][O:34][CH3:33])[N:22]=3)[CH2:14][C@H:13]2[O:30][CH3:31])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Komponenten

4

Edukt 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86648470Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 86648510Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(methoxyimino)methyl-1,3-thiazole-5-carboxylateAusbeute 102,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate obtained by the method described in Example (28a) (100 mg, 0.21 mmol) was dissolved in pyridine (3 mL). Methoxyamine hydrochloride (28 mg, 0.34 mmol) was added, and the mixture was stirred at 60° C. for two hours. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with 1 N hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, ethyl acetate) to obtain 107 mg of the title compound (100%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with 1 N hydrochloric acid and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2a4ea11caf5f4a68bad9f01b97f117fc
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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