1,2-Dichloroethane → 2-{[(4-Fluorophenyl)methyl]oxy}-N-4-pyridazinyl-5-(trifluoromethyl)benzamide

HRID 1623869Notes

Reaction equation

HRID 1623869 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][N:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][C:41]=2[C:42](O)=[O:43])=[CH:34][CH:33]=1>CN(C)C=O.O>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([C:49]([F:50])([F:51])[F:52])=[CH:45][C:41]=2[C:42]([NH:7][C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[O:43])=[CH:34][CH:33]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2984924-AminopyridazineHCID 67107052HCID 67107052, compound

Product 1

HCID 704513632-{[(4-Fluorophenyl)methyl]oxy}-N-4-pyridazinyl-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Pyridazinamine (60.5 mg, 0.64 mmol), EDC (122 mg, 0.64 mmol), HOBT (63.4 mg, 0.41 mmol) and diisopropylethylamine (0.11 ml, 0.64 mmol) were added 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 (20 ml) 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. 70 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-a407db9a4cb04b83930c84b5964999b1
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…