Methylamine → HCID 67158058, compound

HRID 548853Notes

Reaction equation

HRID 548853 reaction equation
C[Al](C)C.[CH3:5][NH2:6].C(O[C:10]([C:12]1[N:13]=[N:14][C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[CH:16][CH:17]=1)=[O:11])C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCOCC1>[CH3:5][NH:6][C:10]([C:12]1[N:13]=[N:14][C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[CH:16][CH:17]=1)=[O:11]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 42630253HCID 42630253, compound

Product 1

HCID 67158058HCID 67158058, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trimethylaluminium (2 M in toluene, 800 □L, 1.6 mmol) was added dropwise (exothermic) to a solution of methylamine (2 M in THF, 800 □L, 1.6 mmol) in dioxane (10 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 6-[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine-3-carboxylic acid ethyl ester (143 mg, 0.4 mmol) in dioxane (5 mL) was added. The resulting mixture was heated at 85-95° C. for 18 h, cooled to room temperature, poured into a sodium potassium tartrate solution and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (122 mg, 99%) which was obtained as a white solid. MS: m/e=343.3 [M+H]−.

Workup

  1. temperatureThe resulting mixture was heated at 85-95° C. for 18 h
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate which
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-a4b5fe07b6a74354946ab8ffa2ed112a
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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