Morpholine → 4-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-morpholine

HRID 548838Notes

Reaction equation

HRID 548838 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH3:15][C:14]1[O:13][N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]=1[CH2:9][O:8][C:5]1[N:4]=[N:3][C:2]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 426297693-Chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 426301354-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-morpholineYield 23%

Conditions

Temperature
116 °C

Procedure

A mixture of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (150 mg, 0.5 mmol) and morpholine (0.17 mL, 2 mmol) was stirred at 116° C. for 4 h. After extraction with ethyl acetate/water the organic phase was concentrated and chromatographed (SiO2, heptane/ethyl acetate=100:0 to 70:30) to afford the title compound as a white solid (40 mg, 23%). MS: m/e=353.3 [M+H]+.

Workup

  1. extractionAfter extraction with ethyl acetate/water the organic phase
  2. concentrationwas concentrated
  3. customchromatographed (SiO2, heptane/ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-99f78ec7c37f465ab7bbcbacbbb07450
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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