Ethanamine, 2,2,2-trifluoro- → HCID 23634409, compound

HRID 551310Notes

Reaction equation

HRID 551310 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].NCC1[CH:26]=[CH:25][C:24]([C:27]2[CH2:31][C:30]([C:36]3[CH:41]=[C:40]([Cl:42])[CH:39]=[C:38]([Cl:43])[CH:37]=3)([C:32]([F:35])([F:34])[F:33])[O:29][N:28]=2)=[CH:23][CH:22]=1>O1CCCC1.C(OCC)(=O)C>[Cl:43][C:38]1[CH:37]=[C:36]([C:30]2([C:32]([F:34])([F:33])[F:35])[O:29][N:28]=[C:27]([C:24]3[CH:23]=[CH:22][C:11]([CH2:12][NH:8][C:1]([NH:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[O:2])=[CH:26][CH:25]=3)[CH2:31]2)[CH:41]=[C:40]([Cl:42])[CH:39]=1

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 682631,1'-CarbonyldiimidazoleHCID 44628234HCID 44628234, compound

Product 1

HCID 23634409HCID 23634409, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a solution of 0.32 g of 1,1′-carbonylbis-1H-imidazole in 7.0 mL of tetrahydrofuran, 0.20 g of 2,2,2-trifluoroethylamine was added, and stirred at room temperature for 1.5 hour. Then, in the reaction mixture, a solution of 0.39 g of 3-[4-(aminomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole synthesized in Step 6 of Synthetic Example 1 in 5.0 mL of tetrahydrofuran was added, and continued to stir at room temperature further for 2.5 hours. After the completion of the reaction, the reaction mixture was diluted with 20 mL of ethyl acetate, washed with water (15 mL×2), and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and the solvent was distilled off under reduced pressure. The residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that was eluted with ethyl acetate-hexane (gradient of 1:8 to 1:1) to obtain 0.43 g of the aimed products as colorless resinous substance.

Workup

  1. stirringto stir at room temperature further for 2.5 hours
  2. customAfter the completion of the reaction
  3. washwashed with water (15 mL×2)
  4. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that
  7. washwas eluted with ethyl acetate-hexane (gradient of 1:8 to 1:1)

Sources & evidence

ORD record
ord-cabc9cda4487472881e09a3f3550d156
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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