Reacción #1509629

Ecuación de reacción

hydrochloric acid

1,4-diamino-2-butanone dihydrochloride

2-amino-4-(3-octylcarbamoyl-propyl)-imidazole-1-carboxylic acid tert-butyl ester

cyanamide

ethanol

→

compound 26

Rendimiento 62.0%

4-(2-amino-ethyl)-1H-imidazol-2-ylamine dihydrochloride

Rendimiento 62.0%

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturabefore heating
2. 2
   Otrothe reaction at 95° C. for 3.5 h while open to the atmosphere
3. 3
   workup.ADDITIONwas added to the flask
4. 4
   Otrothe solution was evaporated to dryness
5. 5
   OtroPurification of the residue by column chromatography (MeOH sat. with NH3/CH2Cl2 90:10)
6. 6
   Otroyielded the product as its corresponding free base
7. 7
   Otrofollowed by evaporation in vacuo

Procedimiento

1,4-diamino-2-butanone dihydrochloride 25 (0.300 g, 1.71 mmol) and cyanamide (0.753 g, 17.9 mmol) were dissolved in water (10 mL). The pH of the solution was adjusted to pH=4.3 before heating the reaction at 95° C. for 3.5 h while open to the atmosphere. After cooling to ambient temperature ethanol (10 mL) was added to the flask and the solution was evaporated to dryness. Purification of the residue by column chromatography (MeOH sat. with NH3/CH2Cl2 90:10) yielded the product as its corresponding free base. Addition of methanol (10 mL) and concentrated hydrochloric acid followed by evaporation in vacuo afforded the target compound 26 (0.211 g, 62%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 6.21 (s, 1H), 5.14 (br s, 2H), 2.81 (m, 2H), 2.47 (m, 2H); HRMS (ESI) calcd for C5H11N4 (MH+) 127.0978, found 127.0977.

Fuente