Acetyl chloride → N-Acetyl-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide

HRID 548818Notes

Reaction equation

HRID 548818 reaction equation
[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.[C:29](Cl)(=[O:31])[CH3:30].C1C[O:36][CH2:35][CH2:34]1>>[C:29]([N: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)[C:35](=[O:36])[CH3:34])(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 426297716-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-ylamine

Product 1

HCID 67157632N-Acetyl-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamideYield 62%

Procedure

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 acetyl chloride (0.067 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. Chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) afforded the title compound (160 mg, 62%) as a light yellow oil. MS: m/e=367.4 [M+H]+.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationwas filtered
  3. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-f6bed9283368463199f625086739f46c
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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