반응 #68502

반응 방정식

N-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

1H-pyrazol-4-ylboronic acid

DMF

potassium carbonate

water

→

N-((6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

반응 조건

후처리

1. 1
   기타A 48 mL sealed tube
2. 2
   기타The tube was flushed with argon
3. 3
   기타sealed
4. 4
   기타placed in a 90° C.
5. 5
   기타for 5 hours
6. 6
   농축The mixture was concentrated
7. 7
   기타the black solid was triturated with water
8. 8
   기타to remove K2CO3
9. 9
   기타purified by column chromatography
10. 10
    세척eluting with 30-70% (90:10:1 DCM:MeOH:NH4OH solution) in DCM over 40 minutes
11. 11
    기타Pure fractions were collected

실험 절차

A 48 mL sealed tube was charged with N-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine (0.150 g, 0.439 mmol), 1H-pyrazol-4-ylboronic acid (0.0737 g, 0.658 mmol), and DMF (3.00 ml, 38.6 mmol). A solution of potassium carbonate (0.182 g, 1.32 mmol) and water (0.696 ml, 38.6 mmol) was added, followed by PdCl2(dppf)-CH2Cl2Adduct (0.0358 g, 0.0439 mmol). The tube was flushed with argon, sealed, then placed in a 90° C. oil bath for 5 hours. The mixture was concentrated and the black solid was triturated with water to remove K2CO3, then purified by column chromatography using a 40 g RediSep column, eluting with 30-70% (90:10:1 DCM:MeOH:NH4OH solution) in DCM over 40 minutes. Pure fractions were collected to give N-((6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine as a white solid.

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