Triethylamine → 2-(4-Fluoro-phenoxy)-N-(5-oxo-morpholin-2-ylmethyl)-nicotinamide

HRID 844059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 844059
Cl.[NH2:2][CH2:3][CH:4]1[CH2:9][NH:8][C:7](=[O:10])[CH2:6][O:5]1.C(N(CC)CC)C.[F:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[N:32]=[CH:31][CH:30]=[CH:29][C:25]=2[C:26](O)=[O:27])=[CH:21][CH:20]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N(CC)CCCl)C>CN(C)C=O.O>[F:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][C:24]2[N:32]=[CH:31][CH:30]=[CH:29][C:25]=2[C:26]([NH:2][CH2:3][CH:4]2[O:5][CH2:6][C:7](=[O:10])[NH:8][CH2:9]2)=[O:27])=[CH:33][CH:34]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 6051232-(4-Fluorophenoxy)nicotinic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 226122616-(Aminomethyl)morpholin-3-one hydrochloride

Produkt 1

HCID 226121642-(4-Fluoro-phenoxy)-N-(5-oxo-morpholin-2-ylmethyl)-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-Aminomethyl-morpholin-3-one hydrochloride (0.200 grams, 1.2 mmole) and triethyl amine (0.150 grams, 1.5 mmole) in dimethylformamide was stirred at room temperature for 30 minutes. To the stirring solution 2-(4-Fluoro-phenoxy)-nicotinic acid (0.280 grams, 1.2 mmole), 1-hydroxybenzotriazole hydrate (0.237 grams, 1.755 mmole) and 2-diethylaminoethyl chloride hydrochloride (0.30 grams, 1.56 mmole) was added and stirred over night. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with 1 N NaOH, water and brine, dried over MgSO4, filtered and concentrated to give a white solid which was purified by chromatography on silica eluting with 5% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave white crystals. (0.175 g); M.P. 157-159° C.; Anal. calcd. for C17H16N3O4F: C, 59.14; H, 4.67; N, 12.17. Found: C, 59.00; H, 4.69; N, 12.19.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with 1 N NaOH, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid which
  7. customwas purified by chromatography on silica eluting with 5% methanol/methylene chloride
  8. customRecrystalization from ethyl acetate/hexane
  9. customgave white crystals

Quellen und Nachweise

ORD-Eintrag
ord-95d764d046904d03849539837fe146f4
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380218B1

Notizen zur Reaktion

Wird geladen…