Isopropylamine → HCID 46897361, compound

HRID 1920947Notes

Reaction equation

HRID 1920947 reaction equation
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].C[O:10][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:22][O:23][C:24]=2[CH2:25][OH:26])[CH:14]=1)=O>CCCCCC.O1CCOCC1>[CH:5]([NH:8][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:22][O:23][C:24]=2[CH2:25][OH:26])[CH:14]=1)=[O:10])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 67492207HCID 67492207, compound

Product 1

HCID 46897361HCID 46897361, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

Trimethylaluminum (0.57 mL of a 2 M solution in hexane, 1.15 mmol) was slowly added to a solution of isopropylamine (68.2 mg, 1.15 mmol) in dioxane (5.0 mL) and stirred at 80° C. for 1 h. Then a solution of 3-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.29 mmol) in dioxane (5.0 mL) was added dropwise. The mixture was stirred at 85° C. overnight. After cooling to room temperature and extractive workup (ethyl acetate/aqueous saturated Seignette's salt solution) the organic phase was dried (Na2SO4) and filtered. Purification by chromatography (silica, ethyl acetate:heptane=3:7 to 1:1) afforded the title compound (50 mg, 46%) as a white solid. MS: m/e=373.9 [M−H]−.

Workup

  1. stirringThe mixture was stirred at 85° C. overnight
  2. temperatureAfter cooling to room temperature
  3. dry with materialextractive workup (ethyl acetate/aqueous saturated Seignette's salt solution) the organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customPurification by chromatography (silica, ethyl acetate:heptane=3:7 to 1:1)

Sources & evidence

ORD record
ord-626204fc973d4051a52cf17287865762
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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