Water → HCID 46872517, compound

HRID 1942273Notes

Reaction equation

HRID 1942273 reaction equation
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].C[O:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:14][CH:13]=1.O>O1CCOCC1>[CH:5]([NH:8][C:11](=[O:10])[C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:14][CH:13]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 46872516HCID 46872516, compound

Product 1

HCID 46872517HCID 46872517, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trimethylaluminium (2 M in toluene, 1.25 mL, 2.0 mmol) was added dropwise (exothermic) to a solution of isopropylamine (210 μL, 2.0 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 1 h. Then 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (200 mg, 0.62 mmol) was added. The resulting mixture was then heated at 90° C. for 2 h and then cooled to room temperature and then poured into water 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 1:4) afforded the title compound (170 mg, 78%) which was obtained as a white solid after trituration from diisopropylether/ethyl acetate. MS: m/e=348.3 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then heated at 90° 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 1:4)

Sources & evidence

ORD record
ord-d8066155bb984a52b01b1731fc078c80
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

Loading…