Triethylamine → 2-Methoxy-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide

HRID 548820노트

반응식

HRID 548820 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][O:14][C:15]1[N:20]=[N:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33]>C1COCC1>[CH3:29][O:30][CH2:31][C:32]([NH:21][C:18]1[N:19]=[N:20][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1)=[O:33]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 426297716-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine

생성물 1

HCID 671577122-Methoxy-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine (200 mg, 0.7 mmol) in THF (4 mL) was added triethylamine (0.12 mL, 0.85 mmol). The mixture was cooled in an ice bath and a solution of methoxyacetyl chloride (0.092 mL, 0.85 mmol) in THF (1 mL) was added dropwise. After stirring for 1 h at room temperature the precipitate was filtered and the organic phase was evaporated. The residue was dissolved in methanol (5 mL), sodium bicarbonate (1 spatula) was added and the mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was extracted (dichloromethane/water). Then the organic phase was dried over sodium sulfate and concentrated. Chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) afforded the title compound (180 mg, 73%) as a white solid. MS: m/e=355.3 [M+H]+.

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationwas filtered
  3. customthe organic phase was evaporated
  4. dissolutionThe residue was dissolved in methanol (5 mL)
  5. additionsodium bicarbonate (1 spatula) was added
  6. stirringthe mixture was stirred at room temperature for 2 h
  7. customThe solvent was evaporated
  8. extractionthe residue was extracted (dichloromethane/water)
  9. dry with materialThen the organic phase was dried over sodium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6979c1f5bfe848d79d43f2d533b004b2
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943619B2

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