Cesium fluoride → 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 15990

반응식

HRID 15990 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1.[F-].[Cs+]>C(#N)C.O>[CH3:22][C:23]1[N:24]=[CH:25][N:26]([C:2]2[N:7]=[C:6]3[N:8]([CH2:11][C:12]4[CH:13]=[C:14]5[C:19](=[CH:20][CH:21]=4)[N:18]=[CH:17][CH:16]=[CH:15]5)[N:9]=[N:10][C:5]3=[N:4][CH:3]=2)[CH:27]=1

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178418800HCID 178418800, 화합물

생성물 1

HCID 248518386-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline수율 56%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
160 °C

실험 절차

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (50 mg, 0.15 mmol), 4-methyl-1H-imidazole (36 mg, 0.44 mmol) and CsF (25 mg, 0.16 mmol) in acetonitrile (1.45 mL) was heated in a microwave to 160° C. for 20 minutes. The reaction was diluted with water (5 mL) and the resulting suspension was filtered. The precipitate was washed with water and then purified by column chromatography using gradient elution with methanol and dichloromethane to afford 6-((6-(4-methyl-1H-imidazol-1-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (28 mg, yield 56%)

후처리

  1. filtrationthe resulting suspension was filtered
  2. washThe precipitate was washed with water
  3. custompurified by column chromatography
  4. washelution with methanol and dichloromethane

출처 및 근거

ORD 기록
ord-c0952ee84e994226b7dcb2797003c9a7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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