Pyridine → HCID 57675191, Verbindung

HRID 490920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490920
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[CH2:7]([N:9]1[C:13]2[N:14]=[CH:15][C:16]([C:25]3[O:29][N:28]=[C:27]([CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:26]=3)=[C:17]([NH:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:12]=2[CH:11]=[N:10]1)[CH3:8].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:7]([N:9]1[C:13]2[N:14]=[CH:15][C:16]([C:25]3[O:29][N:28]=[C:27]([CH2:30][CH:31]4[CH2:36][CH2:35][N:34]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:33][CH2:32]4)[N:26]=3)=[C:17]([NH:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:12]=2[CH:11]=[N:10]1)[CH3:8]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67529443HCID 67529443, Verbindung

Produkt 1

HCID 57675191HCID 57675191, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Methanesulphonyl chloride (1.16 mmol) was added to a stirred solution of Intermediate 125 (0.033 mmol) and pyridine (0.5 ml) in chloroform (1 ml) at room temperature. After stirring at room temperature for 31 h, the reaction mixture was applied to a SPE cartridge (aminopropyl, 5 g) and the cartridge was eluted sequentially with chloroform, ethyl acetate and methanol. Fractions containing the desired product were evaporated in vacuo. The resulting residue was further purified on a SPE cartridge (silica, 1 g) eluting with a gradient of 30-100% ethyl acetate in petroleum ether to afford Example 176. LCMS showed MH+=490, TRET=2.97 min.

Aufarbeitung

  1. washthe cartridge was eluted sequentially with chloroform, ethyl acetate and methanol
  2. additionFractions containing the desired product
  3. customwere evaporated in vacuo
  4. customThe resulting residue was further purified on a SPE cartridge (silica, 1 g)
  5. washeluting with a gradient of 30-100% ethyl acetate in petroleum ether
  6. customto afford Example 176
  7. customMH+=490, TRET=2.97 min.

Quellen und Nachweise

ORD-Eintrag
ord-25299d7b274e4f40b3f12ea1336439f2
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528148B2

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