Methyl N-(triethylammoniosulfonyl)carbamate → Tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

HRID 1616065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616065
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]=[C:10]([CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])[C:9]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=O)(=[O:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClC(Cl)C.O>[F:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH3:20])[C:9]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[C:8]2[C:6]1[O:3][C:1]([CH3:2])=[N:4][N:5]=1

Komponenten

5

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67595345Tert-butyl 1-(4-(2-acetylhydrazinecarbonyl)-6-fluoro-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

Produkt 1

HCID 67595696Tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 1-(4-(2-acetylhydrazinecarbonyl)-6-fluoro-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.553 g, 1.183 mmol) and Burgess reagent (1.128 g, 4.73 mmol) in dichloroethane (11.83 mL) was heated in the microwave at 120° C. for 1 h. The reaction mixture was diluted with water (50 mL) and extracted with DCM (2×50 mL). The organic extracts were washed with brine (1×50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 100% EtOAc in hexane, to provide tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate as a pink solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.61 (1H, d, J=4.3 Hz), 8.22-8.32 (1H, m), 7.80-7.92 (3H, m), 7.36-7.49 (2H, m), 7.17 (1H, d, J=7.0 Hz), 4.88 (1H, t, J=7.1 Hz), 2.34 (3H, s), 1.22-1.38 (12H, m); LC-MS (ESI) m/z 450.1 [M+H]+.

Aufarbeitung

  1. extractionextracted with DCM (2×50 mL)
  2. washThe organic extracts were washed with brine (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with a gradient of 0% to 100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-395d0a699e74407c9df70f739da533e8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765768B2

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