반응 #44281

반응 방정식

tert-butyl methyl{(3R)-1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-yl}carbamate

hydrochloric acid

→

title compound

(3R)—N-methyl-1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-amine

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   세척The organic solution was washed with saturated sodium bicarbonate (5 mL)
2. 2
   기타separated
3. 3
   추출The aqueous solution was extracted with dichloromethane (3×20 mL)
4. 4
   농축concentrated
5. 5
   기타The crude product was purified by flash chromatography
6. 6
   기타a Horizon purification system on a 12M column
7. 7
   세척eluting with chloroform/7 N ammonia in methanol (0.1-3.5%)

실험 절차

To a cooled (0° C.) solution of tert-butyl methyl{(3R)-1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-yl}carbamate (101 mg, 0.219 mmol) in dichloromethane (2.2 mL) was added hydrochloric acid (4 N in dioxane, 1.10 mL, 4.39 mmol). The reaction mixture was allowed to warm to room temperature as the ice bath melted, stirred for 3 hrs, then diluted with dichloromethane (20 mL). The organic solution was washed with saturated sodium bicarbonate (5 mL) and separated. The aqueous solution was extracted with dichloromethane (3×20 mL) and the organics were combined and concentrated. The crude product was purified by flash chromatography using a Horizon purification system on a 12M column eluting with chloroform/7 N ammonia in methanol (0.1-3.5%) to afford the title compound as the free base which was converted to the dihydrochloric acid salt (56 mg, 63%)

출처