Triethylamine → [6-Fluoro-4-(1-methanesulfonyl-piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester

HRID 1929585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929585
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:17][CH2:18][N:19]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:20][CH2:21]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59326737[6-Fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester

Produkt 1

HCID 59326699[6-Fluoro-4-(1-methanesulfonyl-piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [6-fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (80 mg, 0.25 mmol) and methanesulfonyl chloride (58 mg, 0.5 mmol) in tetrahydrofuran (2 mL) was added triethylamine (63.6 mg, 0.63 mmol). After being stirred at room temperature overnight, the mixture was concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 10-50% ethyl acetate in petroleum ether) to afford [6-fluoro-4-(1-methanesulfonyl-piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (82 mg, 83%) as a white solid.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (gradient elution with 10-50% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-734e34c792c947758c6bcf4d3777215a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188090B2

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