Cyclopropanemethanamine → HCID 67157418, compound

HRID 548869Notes

Reaction equation

HRID 548869 reaction equation
C[Al](C)C.[NH2:5][CH2:6][CH:7]1[CH2:9][CH2:8]1.C([O:12][C:13]([C:15]1[N:16]=[N:17][C:18]([O:21][CH2:22][C:23]2[C:24]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[N:25][O:26][C:27]=2[CH3:28])=[CH:19][CH:20]=1)=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCOCC1>[CH:7]1([CH2:6][NH:5][C:13]([C:15]2[N:16]=[N:17][C:18]([O:21][CH2:22][C:23]3[C:24]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)=[N:25][O:26][C:27]=3[CH3:28])=[CH:19][CH:20]=2)=[O:12])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 67157617HCID 67157617, compound

Product 1

HCID 67157418HCID 67157418, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trimethylaluminium (2 M in toluene, 587 μL, 1.2 mmol) was added dropwise (exothermic) to a solution of aminomethylcyclopropane (85 mg, 101 μL, 1.2 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 6-(5-methyl-3-pyridin-4-yl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester (100 mg, 0.29 mmol) in dioxane (4 mL) was added. The resulting mixture was heated at 85-95° C. for 3 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 (78 mg, 73%) which was obtained as a light yellow solid. MS: m/e=366.3 [M+H]−.

Workup

  1. temperatureThe resulting mixture was heated at 85-95° C. for 3 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-62391dae818b46bfb25917faa4f22194
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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