3,5-Dimethylpyridin-2-amine → {1-[4-(6,8-Dimethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 872304

Reaktionsgleichung

Reaktionsgleichung von HRID 872304
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH:19](Br)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][C:30]1[C:31]([NH2:37])=[N:32][CH:33]=[C:34]([CH3:36])[CH:35]=1>C(O)C>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:37]=[C:31]4[C:30]([CH3:29])=[CH:35][C:34]([CH3:36])=[CH:33][N:32]4[C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 30163103,5-Dimethylpyridin-2-amineHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Produkt 1

HCID 66665950{1-[4-(6,8-Dimethyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterAusbeute 14,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

500 mg (1.13 mmol) {1-[4-(2-Bromo-2-phenyl-acetyl)phenyl]-cyclobutyl}-carbamic acid tert.-butyl ester, 137.5 mg (1.13 mmol) 3,5-dimethyl-pyridin-2-yl-amine and molecular sieves (4 Å, dried over night at 120° C. in a drying oven) were heated in 10 mL ethanol in a Dean-Stark apparatus for 23 hours. The reaction mixture had been sucked off via a glass fibre filter and evaporated to dryness. The residue was redissolved in dichloromethane, washed with an 1 M hydrochloric acid, saturated sodium bicarbonate and brine and dried (sodium sulfate). After filtration and removal of the solvent the residue was purified by chromatography on silicagel (eluents: hexane/ethyl acetate) yielding 142.6 mg (25.8%) of the pure title compound and 77.5 mg (14.7%) of the title compound which was slightly contaminated.

Aufarbeitung

  1. filtrationfilter
  2. customevaporated to dryness
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with an 1 M hydrochloric acid, saturated sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationAfter filtration and removal of the solvent the residue
  7. customwas purified by chromatography on silicagel (eluents: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e4b2a8efa28c4287b51bc26e59eccbbb
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975265B2

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