Pyridine → 1,1-Dimethylethyl 4-[4-(4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl)-2-thiazolyl]-1-piperidinecarboxylate

HRID 1802324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802324
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:18][C:19]([C:21]1[CH2:25][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[O:23][N:22]=1)=O.N1C=CC=CC=1>C(O)C>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]1[O:23][N:22]=[C:21]([C:19]2[N:15]=[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[S:16][CH:18]=2)[CH2:25]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 866476752-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone2×

Produkt 1

HCID 666335001,1-Dimethylethyl 4-[4-(4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl)-2-thiazolyl]-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
77 °C

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonylpiperidine-4-carbothioamide (1 g, 4.10 mmol) in ethanol (10 mL) was added 2-chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone (i.e. the product of Step A) (0.99 g) followed by pyridine (0.34 mL, 4.10 mmol). The reaction mixture was heated at 77° C. for 3 h, and then stirred at room temperature overnight. Ethanol was removed from the reaction mixture, and the remaining residue was diluted with ethyl acetate (50 mL). The organic layer was separated, washed with water, saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated under reduced pressure. The resulting oil was purified by column chromatography on silica gel to provide the title compound as a pale yellow sticky oil (1.11 g).

Aufarbeitung

  1. customEthanol was removed from the reaction mixture
  2. additionthe remaining residue was diluted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. washwashed with water, saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oil was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-33fa61845470427fb193f2c7c0f39590
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349870B2

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