Hydrochloric Acid → HCID 86698991, 화합물

HRID 539901

반응식

HRID 539901 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=2)[CH:13]=[N:12]1.Cl>C(O)C>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:2]3[N:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][N:3]=3)=[CH:17][CH:18]=2)[CH:13]=[N:12]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 27680321-methyl-1H-indazol-5-amineHCID 164271482-Chloro-4-(methylthio)pyrimidine

생성물 1

HCID 86698991HCID 86698991, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-chloro-4-(methylthio)pyrimidine (1.0 g, 6.2 mmol) and 1-methyl-1H-indazol-5-amine (1.0 g, 6.8 mmol) in 10 mL of ethanol was added 1 mL of concentrated hydrochloric acid at room temperature. The reaction mixture was heated at 80° C. for 5 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was cooled to room temperature to form a solid. The resulting solid was collected by filtration and rinsed with cold ethanol to afford 1-methyl-N-(4-(methylthio)pyrimidin-2-yl)-1H-indazol-5-amine, intermediate 11 (0.7 g, 41%). The resulting solid was dissolved in 20 mL of dichloromethane and treated with m-chloroperbenzoic acid (mCPBA, 0.9 g, 5.2 mmol) at room temperature. After being stirred for 12 hours at room temperature, the reaction mixture was extracted with dichloromethane (×3) and washed with brine. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was slurrified with heptane and then collected by filtration to afford the desired intermediate 12 as a white solid (0.6 g, 77%).

후처리

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customto form a solid
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed with cold ethanol

출처 및 근거

ORD 기록
ord-63cc732551294189b17ebd8ffdea199f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871778B2

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