반응 #73043

반응 방정식

1-(aminomethyl)cyclohexanol

trimethylorthobutyrate

4-chloro-3-nitroquinoline

4-chloro-3-nitronaphthyridine

trimethylorthoacetate

1-(aminomethyl)cyclobutanol

→

1-[(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol

반응 조건

후처리

1. 1
   기타The crude product was triturated sequentially with ethyl acetate, hot chloroform, and acetonitrile
2. 2
   기타purified by HPFC
3. 3
   세척eluting with a gradient of 0-40% CMA in chloroform
4. 4
   workup.ADDITIONConcentrated hydrochloric acid (2 mL) was added
5. 5
   온도to cool to ambient temperature
6. 6
   기타A precipitate was isolated by filtration
7. 7
   세척washed well with water
8. 8
   기타dried
9. 9
   기타to provide pure product as a white powder, mp>250.0° C

실험 절차

1-[(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol was prepared according to the general methods of Example 57 using 4-chloro-3-nitroquinoline in lieu of 4-chloro-3-nitronaphthyridine and 1-(aminomethyl)cyclobutanol in lieu of 1-(aminomethyl)cyclohexanol in Part A and trimethylorthoacetate in lieu of trimethylorthobutyrate in Part C. The crude product was triturated sequentially with ethyl acetate, hot chloroform, and acetonitrile, purified by HPFC eluting with a gradient of 0-40% CMA in chloroform, and then suspended in water (100 mL). Concentrated hydrochloric acid (2 mL) was added and the mixture was heated to 90° C. The hot solution was made basic (pH 10) with solid sodium bicarbonate. The solution was allowed to cool to ambient temperature. A precipitate was isolated by filtration, washed well with water, and then dried to provide pure product as a white powder, mp>250.0° C. Anal. Calcd for C16H18N4O C, 68.06; H, 6.43; N, 19.84. Found: C, 67.99; H, 6.54; N, 19.81.

출처