반응 #972260

반응 방정식

2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

5-phenyl-1,2,3,4-tetrahydro-2,6-naphthyridine

TFA

Hunig's Base

TBTU

→

TFA

수율 76.0%

1-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-phenyl-3,4-dihydro-2,6-naphthyridin-2(1H)-yl)ethane-1,2-dione

용매

DMF

반응 조건

후처리

1. 1
   기타quenched with 5 mL of water
2. 2
   기타The solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in DMF
4. 4
   기타The DMF solution was purified by prep HPLC
5. 5
   workup.ADDITIONThe fractions containing the expected product
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was further purified by BIOTAGE® flash chromatography

실험 절차

To a suspension of 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (0.124 g, 0.413 mmol) and 5-phenyl-1,2,3,4-tetrahydro-2,6-naphthyridine, TFA (0.147 g, 0.454 mmol) in DMF (5 mL) was added Hunig's Base (0.5 mL, 2.86 mmol) followed by TBTU (0.172 g, 0.537 mmol). The solution was stirred at rt for 5 h and quenched with 5 mL of water. The solvent was removed under reduced pressure and the residue dissolved in DMF and passed through a plug of glass wool. The DMF solution was purified by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure. The residue was further purified by BIOTAGE® flash chromatography using a 0-5% MeOH in dichloromethane gradient. The expected product, 1-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-phenyl-3,4-dihydro-2,6-naphthyridin-2(1H)-yl)ethane-1,2-dione, TFA (0.192 g, 0.314 mmol, 76% yield), was isolated as an off-white solid. LC/MS: m/z 494.12 (M+H)+, 0.878 min (method 6). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.40-12.47 (m, 1H) 9.24 (s, 1H) 8.47-8.58 (m, 1H) 8.25-8.32 (m, 1H) 7.87 (s, 1H) 7.30-7.63 (m, 6H) 4.75-4.96 (m, 2H) 3.59-3.88 (m, 5H) 2.78-2.99 (m, 2H) 2.48-2.52 (m, 3H).

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