Reaktion #638314

Reaktionsgleichung

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

benzyloxyacetyl chloride

TMSI

benzyloxyacetyl chloride

triethylamine

→

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

title compound

Ausbeute 57.4%

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

Ausbeute 57.4%

Lösungsmittel

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 2 min at room temperature
3. 3
   SonstigeCrude product obtained
4. 4
   SonstigeCrude product obtained
5. 5
   Sonstigewas purified by column chromatography

Vorschrift

2-Benzyloxy-N-{2-(8-benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.411 mmol) and benzyloxyacetyl chloride (0.452 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). After stirring 15 min at room temperature, additional benzyloxyacetyl chloride (0.206 mmol, 0.5 eq.) and triethylamine (0.206 mmol, 0.5 eq.) was added. Stirring was continued for 2 min at room temperature and the reaction was worked up as described in the general procedure. 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. Crude product obtained was a brown solid that was purified by column chromatography using 10% acetone/dichloromethane to give the title compound as a tan solid (0.118 mmol, 29% for 2 steps). MS (ESI) m/z 543.4.

Quelle