Реакция #1509629

Уравнение реакции

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

Выход 62.0%

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

Выход 62.0%

Растворители

methanol

water

Условия реакции

Обработка

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

Методика

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.

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