Reaktion #50436

Reaktionsgleichung

2-[2-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid monohydrate

N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride

allylamine

→

benzeneacetamide

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to dryness
2. 2
   SonstigeThe residue was purified by thick layer chromatography
3. 3
   SonstigeThe product was isolated
4. 4
   Sonstigepartitioned between CH2Cl2 and dilute NH4OH
5. 5
   EinengenThe organic phases were concentrated
6. 6
   Sonstigethe residue triturated with hot ethyl acetate
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrates were concentrated
9. 9
   Sonstigethe solid triturated with diethyl ether
10. 10
    Filtrationfiltered

Vorschrift

A mixture of 0.1 g (0.13 mmol) of (E)-5-t2-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]ethyl]-2-[2-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid monohydrate, 0.03 g (0.16 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride, 0.02 mL (4 mmol) of allylamine and 15 mL of dry CH2Cl2 was stirred at room temperature under nitrogen for 18 hours and concentrated to dryness. The residue was purified by thick layer chromatography using ethyl acetate/CH3OH (5:1) as the eluent. The product was isolated and partitioned between CH2Cl2 and dilute NH4OH. The organic phases were concentrated and the residue triturated with hot ethyl acetate and filtered. The filtrates were concentrated and the solid triturated with diethyl ether and filtered to give 60 mg (57%) of (E)-4-[2 -[4-(2-Chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4 ]-diazepin-2-yl]ethyl]-N-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]-phenyl]-2-[2-propenylamino)carbonyl]benzeneacetamide as a tan powder: mp 127-132° C.

Quelle