Reaktion #638316

Reaktionsgleichung

TMSI

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

4-tert-butyl-phenoxyacetyl chloride

→

title compound

Ausbeute 126.6%

2-(4-tert-Butylphenoxy)-N-{2-(5-chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}acetamide

Ausbeute 126.6%

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-tert-butyl-phenoxy)-acetamide

Lösungsmittel

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeCrude product obtained
2. 2
   Sonstigeobtained
3. 3
   Sonstigewas purified by column chromatography

Vorschrift

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-tert-butyl-phenoxy)-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.414 mmol) and 4-tert-butyl-phenoxyacetyl chloride (0.455 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 solid 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 5% methanol/dichloromethane to give the title compound as a white solid (0.262 mmol, 64% for 2 steps). MS (ESI) m/z 585.4.

Quelle