반응 #1017437

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3-(2-(4-methoxybenzylamino)-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide

→

3-(2-amino-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide

용매

TFA

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후처리

1. 1
   농축After concentrating under reduced pressure
2. 2
   기타to remove the TFA
3. 3
   workup.DISSOLUTIONthe oil was dissolved in MeOH
4. 4
   기타purified by reverse phase HPLC

실험 절차

In a sealed tube was combined 3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-N-(cyclohexylmethyl)propanamide (0.32 g, 0.63 mmol, prepared as in Example 3), copper (II) acetate monohydrate (0.025 g, 0.13 mmol), cesium carbonate (0.61 g, 1.9 mmol), hippuric acid (0.016 ml, 0.13 mmol), 2-methyl-/H-imidazole (0.062 g, 0.75 mmol) and DMF (5 mL). The tube was sealed and heated to 140° C. for 48 h. The mixture was cooled to room temperature, transferred to a flask and concentrated to remove the DMF. Adsorbtion onto silica and purification via flash chromatography (slow gradient, 2-10% MeOH/DCM) provided 3-(2-(4-methoxybenzylamino)-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide. Step 2 A solution of 3-(2-(4-methoxybenzylamino)-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide in TFA (10 mL) was heated at 45° C. for 30 min until complete by LC/MS. After concentrating under reduced pressure to remove the TFA, the oil was dissolved in MeOH and purified by reverse phase HPLC to afford 3-(2-amino-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide. MS (ESI, pos. ion) m/z: 392 (M+1).

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