Trifluoroacetic acid → cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

HRID 43975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43975
ClC1N=C(C(N[C@H]2CCN(C3N=NN(CC4C=CC(OC)=CC=4)N=3)C[C@H]2OC)=O)NC=1CC.[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86762084cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

Produkt 1

HCID 86762083cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amideAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide obtained in Example (260a) (28 mg, 0.05 mmol) was dissolved in anisole (1 mL). Trifluoroacetic acid (2 mL) was added, and the mixture was stirred at 45° C. for 3.5 hours. Following concentration under reduced pressure, the reaction solution was diluted and extracted with dichloromethane and aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was solidified by adding chloroform and hexane to obtain 4.1 mg of the title compound as a white solid (20%).

Aufarbeitung

  1. concentrationconcentration under reduced pressure
  2. additionthe reaction solution was diluted
  3. extractionextracted with dichloromethane and aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionby adding chloroform and hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b4693a0466b433bacb635cee146a4db
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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