Oxolan-3-amine → HCID 67158054, compound

HRID 548859Notes

Reaction equation

HRID 548859 reaction equation
C[Al](C)C.[NH2:5][CH:6]1[CH2:10][O:9][CH2:8][CH2:7]1.C(O[C:14]([C:16]1[N:17]=[N:18][C:19]([O:22][CH2:23][C:24]2[C:25]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[N:26][O:27][C:28]=2[CH3:29])=[CH:20][CH:21]=1)=[O:15])C.[C:37](C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCOCC1>[O:9]1[CH2:8][CH2:7][CH:6]([NH:5][C:14]([C:16]2[N:17]=[N:18][C:19]([O:22][CH2:23][C:24]3[C:25]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=4)=[N:26][O:27][C:28]=3[CH3:29])=[CH:20][CH:21]=2)=[O:15])[CH2:10][CH2:37]1

Participants

6

Reactant 4

HCID 3365553Oxolan-3-amineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 42630253HCID 42630253, compound

Product 1

HCID 67158054HCID 67158054, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trimethylaluminium (2 M in toluene, 800 μL, 1.6 mmol) was added dropwise (exothermic) to a solution of 4-aminotetrahydrofuran (162 mg, 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 then heated at 85-95° C. for 4 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 0:100) afforded the title compound (146 mg, 89%) which was obtained as an off white solid. MS: m/e=413.1 [M+H]−.

Workup

  1. temperatureThe resulting mixture was then heated at 85-95° C. for 4 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 0:100)

Sources & evidence

ORD record
ord-80ce4173094249dfa85bae83b85fb8ba
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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