Pentafluorophenol → HCID 72544690, compound

HRID 526695Notes

Reaction equation

HRID 526695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:25][O:26][C:27]([CH3:32])([CH3:31])[C:28](O)=[O:29])[C:11]([CH3:24])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=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:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:25][O:26][C:27]([CH3:32])([CH3:31])[C:28]([NH:57][CH2:58][C:59]3[CH:60]=[CH:61][C:62]([C:63]([OH:65])=[O:64])=[CH:66][CH:67]=3)=[O:29])[C:11]([CH3:24])=[N:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 13041PentafluorophenolHCID 655264-(Aminomethyl)Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 72544687HCID 72544687, compound

Product 1

HCID 72544690HCID 72544690, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 280 mg of 2-[5-(4-Chloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-2-methyl-propionic acid in 3 ml of DMF, 138 mg of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 133 mg of pentafluorophenol and 392 mg of NEM were added and the reaction mixture was stirred for 2 h at room temperature. Then, 180 mg of 4-Aminomethyl-benzoic acid and 300 mg of NEM in 5 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: 36 mg.

Workup

  1. waitAfter 16 h
  2. filtrationfiltered through a chem Elut® cartridge
  3. washby eluting with ethyl acetate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was purified by preparative HPLC (
  6. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  7. additionThe fractions containing the product
  8. customwere evaporated
  9. customto yield a white solid

Sources & evidence

ORD record
ord-b0b8334902cb4f1697af4b06df39bfd2
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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