Triethylamine → N-(2-Pyridylmethyl)-4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzamide

HRID 2395072Notizen

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][C:14]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzoic acid (0.48 g, 1.44 mmol) and 2-aminomethylpyridine (0.189 g, 1.748 mmol) were dissolved in DMF (20 ml) and cooled to 0° C. Triethylamine (0.15 g, 1.5 mmol) was added followed by diphenylphosphorylazide (0.41 g, 1.48 mmol). The reaction mixture was stirred under argon and allowed to warm to ambient temperature overnight. The reaction was partitioned between EtOAc/water, the organic phase was washed with aqueous sodium bicarbonate, water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (MeOH/CH2Cl2) followed by recrystallisation from EtOAc/hexane and then from EtOH/water to give the title product.

Aufarbeitung

temperatureto warm to ambient temperature overnight
customThe reaction was partitioned between EtOAc/water
washthe organic phase was washed with aqueous sodium bicarbonate, water
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by flash chromatography (MeOH/CH2Cl2)
customfollowed by recrystallisation from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-e771f3f386ff4f268896a13d963552a4
Quelldatensatz: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05811459

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