Sodium hydride → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 548888

반응식

HRID 548888 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[H-].[Na+].Cl[C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH:24]=[N:25][N:26]=2)[N:23]=1>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH:24]=[N:25][N:26]=2)[N:23]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazineHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

생성물 1

HCID 426302496-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (100 mg, 0.53 mmol) in DMF (2 mL) was added sodium hydride (55% dispersion in mineral oil, 25.4 mg, 0.58 mmol). The mixture was stirred at room temperature for 15 min. After addition of 6-chloro-1,2,4-triazolo[4,3-b]pyridazine (90 mg, 0.58 mmol) the mixture was stirred at room temperature for another 2 h. Then the mixture was evaporated, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Chromatography (SiO2, dichloromethane:methanol=100:0 to 9:1) afforded the title compound (80 mg, 51%) as a white solid. MS: m/e=308.4 [M+H]+.

후처리

  1. stirringwas stirred at room temperature for another 2 h
  2. customThen the mixture was evaporated
  3. extractionextracted (ethyl acetate/water)
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-92ae9d6cfb8e4f08b0f53649947e0ec7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943619B2

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