反応 #1509629

反応方程式

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

収率 62.0%

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

収率 62.0%

溶媒

methanol

water

反応条件

後処理

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

実験手順

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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