Diisopropylethylamine → {6-Fluoro-4-[1-(pyridine-3-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 2363832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363832
C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([S:45](Cl)(=[O:47])=[O:46])[CH:40]=1>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([S:45]([C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)(=[O:47])=[O:46])[CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 86686887HCID 86686887, Verbindung

Produkt 1

HCID 86686895{6-Fluoro-4-[1-(pyridine-3-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl esterAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Diisopropylethylamine (0.3 mL, 1.7 mmol) was added at 0° C. to a solution of (6-fluoro-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 150 mg, 0.36 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 minutes and then a solution of pyridine-3-sulfonyl chloride (which may be prepared as described above; 320 mg, 1.8 mmol) in CH2Cl2 (1 mL) was added. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using a Biotage purification system, eluting with 30% ethyl acetate/hexanes, to give {6-fluoro-4-[1-(pyridine-3-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (85 mg, 53%) as a sticky white solid. MS cald. for C23H24FN2O4S [(M+H)+]: 443, obsd. 443.2.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel using
  4. customa Biotage purification system
  5. washeluting with 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5941b0675d3d421a925bcb4c4320643d
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691993B2

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