1,2-Dichloroethane → 2-{[(4-fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(trifluoromethyl)benzamide

HRID 1623870Notes

Reaction equation

HRID 1623870 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:11]=2[C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=[CH:29][C:30]2[N:35]([OH:36])N=[N:33][C:31]=2[CH:32]=1.CC1C(N)=CON=1.CCN(C(C)C)C(C)C>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:11]=2[C:12]([NH:33][C:31]2[C:30]([CH3:29])=[N:35][O:36][CH:32]=2)=[O:14])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 138042843-Methyl-1,2-oxazol-4-amineHCID 67107052HCID 67107052, compound

Product 1

HCID 671076762-{[(4-fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-(trifluoromethyl)benzoic acid (may be prepared as described in Description 119; 100 mg, 0.32 mmol in N,N-dimethylformamide (4 ml) was added EDC (122 mg, 0.64 mmol), HOBT (63.4 mg, 0.41 mmol), 3-methyl-4-isoxazolamine (86 mg, 0.64 mmol), DIPEA (0.22 ml, 1.27 mmol) and the mixture was stirred at room temperature overnight. The mixture was then heated to 70° C. overnight (NOTE: it would be better to prepare the acid chloride and react this with the amine). The mixture was diluted with water (25 ml) and extracted with ethyl acetate (3×25 ml). The organics were combined, evaporated under reduced pressure on a buchi and the residue was purified using an MDAP to yield the title compound. 33 mg.

Workup

  1. temperatureThe mixture was then heated to 70° C. overnight (NOTE
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. customevaporated under reduced pressure on a buchi
  4. customthe residue was purified

Sources & evidence

ORD record
ord-5bcefb252be7464097ea1b8a917a19df
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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