تفاعل #332046

معادلة التفاعل

p-toluenesulfonyl chloride

3-Chloroperoxybenzoic acid

N-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide

ammonium hydroxide

→

N-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled in an ice bath
2. 2
   workup.STIRRINGAfter 15 minutes of stirring
3. 3
   workup.STIRRINGthe reaction mixture was stirred for 72 hours
4. 4
   أخرىThe fractions were separated
5. 5
   استخلاصthe aqueous fraction was extracted with chloroform
6. 6
   غسيلThe combined organic fractions were washed with brine
7. 7
   أخرىpurified by chromatography
8. 8
   غسيلeluting with a linear gradient of 2-20% CMA in chloroform)
9. 9
   أخرىRecrystallization from acetonitrile

الإجراء التجريبي

3-Chloroperoxybenzoic acid (60% pure, 0.283 g, 1.0 mmol) was added to a solution of N-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide (0.380 g, 1.0 mmol) in chloroform (10 mL) and the reaction was stirred for 1 hour. The mixture was cooled in an ice bath and ammonium hydroxide (3 mL) was added. After 15 minutes of stirring, p-toluenesulfonyl chloride (0.190 g, 1.0 mmol) was added and the reaction mixture was stirred for 72 hours. The fractions were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were washed with brine and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a linear gradient of 2-20% CMA in chloroform). Recrystallization from acetonitrile provided 0.231 g of N-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]-2-methylpropanamide as an off-white solid, mp 259-261° C.

المصدر