Butyric Acid → 1-(3-Fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidin-1-yl)butan-1-one

HRID 1961552Notes

Reaction equation

HRID 1961552 reaction equation
[F:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH2:16][C:15]([C:21]4[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[C:23]([Cl:29])[CH:22]=4)([C:17]([F:20])([F:19])[F:18])[O:14][N:13]=3)=[CH:8][CH:7]=2)[CH2:5][NH:4][CH2:3]1.[C:30](O)(=[O:34])[CH2:31][CH2:32][CH3:33].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[F:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH2:16][C:15]([C:21]4[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[C:23]([Cl:29])[CH:22]=4)([C:17]([F:19])([F:20])[F:18])[O:14][N:13]=3)=[CH:8][CH:7]=2)[CH2:3][N:4]([C:30](=[O:34])[CH2:31][CH2:32][CH3:33])[CH2:5]1

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 781477423-(4-(3-Fluoroazetidin-3-yl)phenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 566506341-(3-Fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidin-1-yl)butan-1-oneYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(4-(3-fluoroazetidin-3-yl)phenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (0.05 mmol) was dissolved in dimethyl formamide (0.5 mL); this was added to butyric acid (0.1 mmol), followed by a solution of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate in dimethyl formamide (0.5 mL), and triethylamine (0.5 mmol). The resulting mixture was shaken at ambient temperature for 16 hours. The solvent was removed by distillation under vacuum, and the crude product purified by preparative HPLC to give 3.2 mg of 1-(3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidin-1-yl)butan-1-one. MH+ 537; retention time 9.83 minutes.

Workup

  1. customThe solvent was removed by distillation under vacuum
  2. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-eb91e925e79f4891bcc79cfc93690e99
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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