Triethylamine → Methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-chloronicotinate

HRID 384635

Reaktionsgleichung

Reaktionsgleichung von HRID 384635
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[CH:3]=1.[NH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C(N(CC)CC)C>C(O)CCC>[C:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][CH:15]([CH2:14][NH:13][C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([Cl:12])[CH:3]=2)[CH2:16][CH2:17]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 2764083Methyl4,6-dichloronicotinate

Produkt 1

HCID 59613527Methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-chloronicotinateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4,6-dichloronicotinate (1.20 g, 5.8 mmol), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (1.24 g, 5.8 mmol) and triethylamine (4.09 mL, 29.1 mmol) in n-butanol (13 mL) was heated at 120° C. for 90 minutes by microwave irradiation. The solvent was evaporated and the mixture was purified by flash chromatography on silica, eluting with ethyl acetate-hexane (1:4), to give methyl 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-chloronicotinate as a colourless solid (1.87 g, 84%).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe mixture was purified by flash chromatography on silica
  3. washeluting with ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-d1c25a87136f4da48b4315d47e77ff47
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367658B2

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