Morpholine → HCID 86721319, Verbindung

HRID 1777077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777077
Cl[S:2]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[O:18]1[CH2:19][CH2:20][N:15]([S:2]([C:5]2[CH:6]=[N:7][CH:8]=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3])[CH2:16][CH2:17]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 545939885-Chlorosulfonyl-nicotinic acid methyl ester

Produkt 1

HCID 86721319HCID 86721319, VerbindungAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 5-(chlorosulfonyl)nicotinate (35 mg, 0.149 mmol) was added to the morpholine (25.9 mg, 0.297 mmol) in presence of Potassiumcarbonate (41.1 mg, 0.297 mmol) in THF (8 mL) at room temperature and the reaction mixture was stirred for 12 h at room temperature. The reaction was monitored by TLC, after completion of the reaction, Solvent was removed by vacuum and then compound was purified by column chromatography (2% Methanol/DCM) afforded the product methyl 5-(morpholinosulfonyl)nicotinate (26 mg, 0.090 mmol, 60.5% yield) as a solid. 1HNMR (400 MHz, CDCl3): δ 9.41 (s, 1H), 9.12 (s, 1H), 8.60 (d, 1H, J=2.0 Hz), 4.01 (s, 3H), 3.76 (m, 4H), 3.07 (m, 4H).

Aufarbeitung

  1. customafter completion of the reaction, Solvent
  2. customwas removed by vacuum
  3. customcompound was purified by column chromatography (2% Methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bb535f1e41a24a6c8bed6833d8b610ec
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266838B2

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