Ethanolamine → HCID 42630132, compound

HRID 548855Notes

Reaction equation

HRID 548855 reaction equation
C[Al](C)C.[CH2:5]([CH2:7][NH2:8])[OH:6].C([O:11][C:12]([C:14]1[N:15]=[N:16][C:17]([O:20][CH2:21][C:22]2[C:23]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:24][O:25][C:26]=2[CH3:27])=[CH:18][CH:19]=1)=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCOCC1>[OH:6][CH2:5][CH2:7][NH:8][C:12]([C:14]1[N:15]=[N:16][C:17]([O:20][CH2:21][C:22]2[C:23]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:24][O:25][C:26]=2[CH3:27])=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 42630253HCID 42630253, compound

Product 1

HCID 42630132HCID 42630132, compoundYield 24.2%

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 ethanolamine (96 μL, 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 2 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 (36 mg, 24%) which was obtained as a white solid. MS: m/e=373.1 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then heated at 85-95° C. for 2 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-8e6e22a8464646e1ab53214fdca73c3b
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

Loading…