1,1'-Carbonyldiimidazole → 4-[4-(4-Bromo-3-trifluoromethoxy-phenylcarbamoyl)-piperazin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1500521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500521
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].C1N=CN([C:19](N2C=NC=C2)=[O:20])C=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[CH2:44][CH2:43][N:42]([C:19](=[O:20])[NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([O:9][C:10]([F:12])([F:11])[F:13])[CH:4]=3)[CH2:41][CH2:40]2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 141291984-Bromo-3-(trifluoromethoxy)anilineHCID 17750358tert-Butyl 4-(piperazin-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 867005114-[4-(4-Bromo-3-trifluoromethoxy-phenylcarbamoyl)-piperazin-1-yl]-piperidine-1-carboxylic acid tert-butyl esterAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3-trifluoromethoxy-phenylamine (500 mg, 2 mmol) in DCM (5 mL) was added N,N-carbonyldiimidazole (348 mg, 2.15 mmol). The reaction mixture was stirred at RT overnight and then 4-piperazin-1-yl-piperidine-1-carboxylic acid tert-butyl ester (579 mg, 2.15 mmol, Preparation 12) was added and the reaction mixture was stirred at RT for 15 min, and concentrated by rotary evaporation and purified by silica gel chromatography (80 g silica, 0-10% MeOH/DCM) to provide the title intermediate (776 mg, 70% yield) as a yellow powder. (m/z): [M+H]+ calcd for C22H30BrF3N4O4 551.14, found 551.3.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at RT for 15 min
  2. concentrationconcentrated by rotary evaporation
  3. custompurified by silica gel chromatography (80 g silica, 0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c7ebaa574e6b4571b73cbee04e231b47
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206159B2

Notizen zur Reaktion

Wird geladen…