Pentafluorophenol → HCID 72202148, compound

HRID 526713Notes

Reaction equation

HRID 526713 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[C:12]([CH3:24])[C:11]([CH2:25][O:26][C:27]([CH3:32])([CH3:31])[C:28](O)=[O:29])=[N:10]1.Cl.CN(C)CCCN=C=NCC.FC1C(O)=C(F)C(F)=C(F)C=1F.[NH2:57][CH2:58][C:59]1[CH:67]=[CH:66][C:62]([C:63]([OH:65])=[O:64])=[CH:61][CH:60]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)=[C:12]([CH3:24])[C:11]([CH2:25][O:26][C:27]([CH3:32])([CH3:31])[C:28]([NH:57][CH2:58][C:59]2[CH:60]=[CH:61][C:62]([C:63]([OH:65])=[O:64])=[CH:66][CH:67]=2)=[O:29])=[N:10]1

Participants

7

Reactant 4

HCID 13041PentafluorophenolHCID 655264-(Aminomethyl)Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89906548HCID 89906548, compound

Product 1

HCID 72202148HCID 72202148, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 600 mg of 2-[1-(2,4-Dichloro-phenyl)-4-methyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-2-methyl-propionic acid in 9 ml of DMF, 283 mg of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 271 mg of pentafluorophenol and 300 mg of NEM was added and the reaction mixture was stirred for 3 h at room temperature. Then, 278 mg of 4-Aminomethyl-benzoic acid and 424 mg of NEM in 10 ml of DMF were added. After 16 h the reaction mixture was diluted with water and filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid. Yield: 204 mg.

Workup

  1. filtrationfiltered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was purified by preparative HPLC (
  5. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  6. additionThe fractions containing the product
  7. customwere evaporated
  8. customto yield a white solid

Sources & evidence

ORD record
ord-0f34bca9546b4197a51fbf00bf6450d4
Source dataset
uspto-grants-2016_05
Patent number
US09346762B2

Reaction notes

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