Allylamine → Benzeneacetamide

HRID 22158

Reaktionsgleichung

Reaktionsgleichung von HRID 22158
O.C1(C2N=C(C=CC3C=C([NH:19][C:20](=[O:31])[CH2:21][C:22]4[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=4C(O)=O)C=CC=3)SC=2)CCC1.Cl.C(N=C=NCCCN(C)C)C.C(N)C=C>C(Cl)Cl>[C:22]1([CH2:21][C:20]([NH2:19])=[O:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:23]=1

Komponenten

5

Edukt 3

HCID 7853AllylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1317190282-[2-[3-[2-(4-Cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid monohydrate

Produkt 1

HCID 7680Benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by thick layer chromatography
  3. customThe product was isolated
  4. custompartitioned between CH2Cl2 and dilute NH4OH
  5. concentrationThe organic phases were concentrated
  6. customthe residue triturated with hot ethyl acetate
  7. filtrationfiltered
  8. concentrationThe filtrates were concentrated
  9. customthe solid triturated with diethyl ether
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-69af79e665f04f5092f121a75d85560c
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428004

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