Methyl iodide → N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)-N-methylacetamide

HRID 1624902노트

반응식

HRID 1624902 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:17]=[C:18]([NH:22][C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][CH:21]=3)[C:8]2=[O:26])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I>C1COCC1.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:14][CH3:15])=[N:10][N:9]([C:16]3[CH:17]=[C:18]([N:22]([CH3:31])[C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][CH:21]=3)[C:8]2=[O:26])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59139822N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

생성물 1

HCID 59139848N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)-N-methylacetamide수율 76.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

According to Scheme 9 Step 1: To a solution of N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (70 mg, 0.17 mmol) in THF (3 mL) was added portionwise at 0° C. sodium hydride (55%) 11 mg, 0.26 mmol). The suspension was stirred 10 minutes at room temperature. Then, methyl iodide (87 μl, 1.40 mmol) was added dropwise and the reaction mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was diluted with 100 mL of a saturated solution of ammonium chloride and the aqueous layer was extracted twice with 100 mL of DCM. The organic layers were combined to be successively dried over MgSO2, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2) using CH2Cl2/MeOH 99/1 as eluant to afford N-(3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)-N-methylacetamide (54 mg, 75%) as a white solid.

후처리

  1. stirringthe reaction mixture was stirred at room temperature under nitrogen atmosphere overnight
  2. extractionthe aqueous layer was extracted twice with 100 mL of DCM
  3. dry with materialto be successively dried over MgSO2
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a brown solid
  7. customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2)

출처 및 근거

ORD 기록
ord-2fc35075699a4d8bb30a0284225ca6ab
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779129B2

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