2,6-Lutidine → Methyl 2-(4-cyclopropanecarboxamido-phenylsulfanyl)-5-nitro-6-(5-methylpyrazol-3-ylamino)-4-pyrimidinecarboxylate

HRID 1689742노트

반응식

HRID 1689742 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-:14])=[O:13])=[C:4](Cl)[N:3]=1.N1C(C)=CC=CC=1C.[NH2:24][C:25]1[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=1.[CH:31]1([C:34]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][CH:38]=2)=[O:35])[CH2:33][CH2:32]1>O1CCOCC1.C(OCC)(=O)C>[CH:31]1([C:34]([NH:36][C:37]2[CH:38]=[CH:39][C:40]([S:43][C:2]3[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([NH:24][C:25]4[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=4)[N:3]=3)=[CH:41][CH:42]=2)=[O:35])[CH2:32][CH2:33]1

참가 물질

7

반응물 4

HCID 79372,6-LutidineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 10586879Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 16722082N-(4-mercaptophenyl)cyclopropanecarboxamide

생성물 1

HCID 59781444Methyl 2-(4-cyclopropanecarboxamido-phenylsulfanyl)-5-nitro-6-(5-methylpyrazol-3-ylamino)-4-pyrimidinecarboxylate수율 70%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To compound 3 (1.00 g, 3.76 mmol, 1 equiv) and 2,6-lutidine (1.31 mL, 11.25 mmol, 3 equiv) in dioxane (5 mL) at room temperature was added 3-amino-5-methyl-pyrazol (0.38 g, 3.95 mmol, 1.05 equiv, in 5 mL dioxane) drop wise. After stirring at room temperature for 0.5 hr, 4-cyclopropanecarboxamido-thiophenol (0.87 g, 4.5 mmol, 1.2 equiv) was added. The reaction was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate and washed with 1 N HCl (50 mL) and saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure, and purified by flash column chromatography to yield compound 6 as a yellow solid (1.2 g, 70%).

후처리

  1. stirringThe reaction was stirred at room temperature for overnight
  2. washwashed with 1 N HCl (50 mL) and saturated NaHCO3 (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-71760296051d4ecd886eba2cf9ddc15d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153630B2

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