Hydrochloric Acid → 2-Bromo-5-[(4-chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410113
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)O)=[O:5])[CH3:2].[NH2:24][CH:25]1[CH2:30][N:29]([CH3:31])[C:28](=[O:32])[CH2:27][CH2:26]1.Cl>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[NH:24][CH:25]1[CH2:26][CH2:27][C:28](=[O:32])[N:29]([CH3:31])[CH2:30]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 510721765-Amino-1-methylpiperidin-2-oneHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate2×

Produkt 1

HCID 867077672-Bromo-5-[(4-chloro-phenyl)-(1-methyl-6-oxo-piperidin-3-ylamino)-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The title compound was prepared in analogy to the procedure described for step E2 using 2-bromo-5-[(4-chlorophenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (intermediate B) and 5-amino-1-methylpiperidin-2-one (ChemBridge, free base was made from the purchased HCl salt) as starting materials. The crude reaction mixture was diluted with EtOAc and washed with aqueous NaHCO3 solution and brine. tr: 1.07 min (LC-MS 2); ESI-MS: 511.1 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.42 (m, 2H), 7.30 (m, 2H), 6.28 (NH, br, 1H), 4.85-5.00 (m, 1 H), 4.25 (quin, 2 H), 3.15-3.05 (m, 2H), 2.84-2.75 (m, 1H), 2.72 (d, 3H), 2.38-1.85 (m, 4H), 1.75-1.58 (m, 1), 1.45 (d, 3 H), 1.24 (t, 3 H), 0.83 (t, 3H).

Aufarbeitung

  1. customThe crude reaction mixture
  2. washwashed with aqueous NaHCO3 solution and brine
  3. custom1.07 min (LC-MS 2)

Quellen und Nachweise

ORD-Eintrag
ord-f64b30b3576f498ea11f35cef7a3b6f6
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815926B2

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