Reaktion #638313

Reaktionsgleichung

Ethyl acetate

2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine

phenoxyacetyl chloride

TMSI

→

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-phenoxy-acetamide

title compound

Ausbeute 84.7%

N-{2-(5-Chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}-2-phenoxyacetamide

Ausbeute 84.7%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeCrude product obtained
2. 2
   workup.STIRRINGthe reaction was stirred 3 h at 70° C. after which time the reaction
3. 3
   Sonstigewas quenched
4. 4
   SonstigeCrude product obtained
5. 5
   Sonstigewas purified by column chromatography
6. 6
   Einengenfollowed by concentration
7. 7
   Waschenwashing the solid with diethyl ether (3×5 mL)

Vorschrift

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-phenoxy-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.404 mmol) and phenoxyacetyl chloride (0.445 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). Ethyl acetate was used in place of dichloromethane in the workup procedure. Crude product obtained was a white foam that was subjected to the conditions described above for TMSI-mediated O-benzyl deprotection. After stirring 16 h at 70° C., 1,2-dichloroethane (5.6 mL) was added and the reaction was stirred 3 h at 70° C. after which time the reaction was quenched and worked up as described above. Crude product obtained was a brown oil that was purified by column chromatography using 10% acetone/dichloromethane followed by concentration and washing the solid with diethyl ether (3×5 mL) to give the title compound as a tan solid (0.171 mmol, 42% for 2 steps). MS (ESI) m/z 529.4.

Quelle