Nicotinic Acid → [(Pyridine-3-carbonyl)-amino]-acetic acid 4-allyl-2-methoxy-phenyl ester

HRID 82492

Reaktionsgleichung

Reaktionsgleichung von HRID 82492
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:14])[CH2:12][NH2:13])=[C:6]([O:15][CH3:16])[CH:5]=1)[CH:2]=[CH2:3].[CH:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:23](O)=[O:24])[CH:18]=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:14])[CH2:12][NH:13][C:23]([C:19]2[CH:20]=[N:21][CH:22]=[CH:17][CH:18]=2)=[O:24])=[C:6]([O:15][CH3:16])[CH:5]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 938Nicotinic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69920127Amino-acetic acid 4-allyl-2-methoxy-phenyl ester

Produkt 1

HCID 53340886[(Pyridine-3-carbonyl)-amino]-acetic acid 4-allyl-2-methoxy-phenyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of Amino-acetic acid 4-allyl-2-methoxy-phenyl ester (510 mg, 1.7 mmol), in DCM (20 mL) were added niacin (0.23 g, 1.9 mmol), N-methyl morpholine (0.96 mL, 8.8 mmol), EDC.HCl (0.67 g, 3.5 mmol) at ice temperature (0° C.). The mixture was allowed to stir at room temperature (25° C.) over a period of 2 hrs. The resulting mixture was diluted with DCM (200 mL) washed with water (2×100 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was purified by silica gel column chromatography to obtain product as off-white solid (210 mg, 43%).

Aufarbeitung

  1. washwashed with water (2×100 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained upon evaporation of the solvent
  4. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f7e798326e974114812ded31a5c65c31
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846721B2

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