Pyridine → 8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate

HRID 38493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38493
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].N1C=CC=CC=1.[CH:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[C:32]([C:35]([N:37]2[CH2:42][CH2:41][C:40]4([CH2:51][C:50](=[O:52])[C:49]5[C:44](=[CH:45][CH:46]=[C:47]([C:53]6[CH:54]=[N:55][N:56]([CH3:58])[CH:57]=6)[CH:48]=5)[O:43]4)[CH2:39][CH2:38]2)=[O:36])[CH:31]=[C:30]3O)[CH2:24][CH2:23]1>C(Cl)(Cl)Cl.O>[F:6][C:5]([F:8])([F:7])[S:2]([O:1][C:30]1[C:29]2[C:34](=[C:25]([CH:22]3[CH2:24][CH2:23]3)[CH:26]=[CH:27][CH:28]=2)[N:33]=[C:32]([C:35]([N:37]2[CH2:38][CH2:39][C:40]3([CH2:51][C:50](=[O:52])[C:49]4[C:44](=[CH:45][CH:46]=[C:47]([C:53]5[CH:54]=[N:55][N:56]([CH3:58])[CH:57]=5)[CH:48]=4)[O:43]3)[CH2:41][CH2:42]2)=[O:36])[CH:31]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178480023HCID 178480023, Verbindung

Produkt 1

HCID 582086748-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Tf2O (0.224 ml, 1.327 mmol) was added to a stirred solution of pyridine (0.358 ml, 4.42 mmol) and 1′-[(8-cyclopropyl-4-hydroxyquinolin-2-yl)carbonyl]-6-(1-methyl-1H-pyrazol-4-yl)spiro[chroman-2,4′-piperidin]-4-one (450 mg, 0.885 mmol) in CHCl3 (4.5 ml) at −50° C. and the mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with CHCl3 and H2O, the organic layer was washed with brine and dried over MgSO4. After filtration and concentration, the residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound as a pale yellow solid.

Aufarbeitung

  1. washthe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by silicagel column chromatography (hexane/EtOAc)
  5. customto give

Quellen und Nachweise

ORD-Eintrag
ord-c89b23b179364bc7a3e2309a61b7760f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524730B2

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