Water → HCID 25131099, compound

HRID 2262537Notes

Reaction equation

C[Al](C)C.[CH:5]1([CH2:8][NH2:9])[CH2:7][CH2:6]1.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([C:24]3[C:25]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[N:26][O:27][C:28]=3[C:29]([F:32])([F:31])[F:30])[N:21]=[CH:20]2)=[CH:15][CH:14]=1.O>O1CCOCC1>[CH:5]1([CH2:8][NH:9][C:12](=[O:11])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[C:22]([C:24]4[C:25]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)=[N:26][O:27][C:28]=4[C:29]([F:32])([F:31])[F:30])[N:21]=[CH:20]3)=[CH:15][CH:14]=2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of trimethylaluminium (2 M in toluene, 338 μL, 0.68 mmol) and cyclopropanemethylamine (60.4 μL, 0.68 mmol) in dioxane (9 mL) was stirred at room temperature for 1 h and then a solution of 4-[4-(3-phenyl-5-trifluoromethyl-isoxazol-4-yl)-imidazol-1-yl]-benzoic acid methyl ester (70 mg, 0.17 mmol) in dioxane (6 mL) was added. The resulting mixture was then heated at 85-95° C. overnight 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 sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=60:40) afforded the title compound (60 mg, 78%) which was obtained as a colourless oil. MS: m/e=453.3 [M+H]+.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate which
washwas then washed with brine
dry with materialdried over sodium sulphate
customevaporated
customPurification by chromatography (SiO2, heptane:ethyl acetate=60:40)

Sources & evidence

ORD record: ord-2446760d8edd43b59cb75934d820eb8f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851469B2

Reaction notes

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