Acetyl chloride → [4-(1-Acetyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester

HRID 1929586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929586
[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.[C:24](Cl)(=[O:26])[CH3:25]>O1CCCC1.CN(C)C1C=CN=CC=1>[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]([C:24](=[O:26])[CH3:25])[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 2

HCID 6367Acetyl chlorideHCID 59326737[6-Fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester

Produkt 1

HCID 59326711[4-(1-Acetyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of [6-fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (the intermediate for example 4-1, 1st step, 80 mg, 0.25 mmol) and acetyl chloride (39 mg, 0.5 mmol) in tetrahydrofuran (2 mL) was added a solution of 4-dimethylaminopyridine (76 mg, 0.63 mmol) in tetrahydrofuran (1 mL) dropwise. 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 [4-(1-acetyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester (72 mg, 79%) 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-439472cb626f4803904ad4a078563ea0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188090B2

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