Tetrahydrofuran → N-{5-[(5-aminopyridin-2-yl)(methyl)amino]-2-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 2366750Notes

Reaction equation

HRID 2366750 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([N:12]([CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)[CH:9]=[CH:8][C:7]=1[F:23])=[O:4].O1CCCC1>C(O)C.[C].[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]([CH3:22])[C:10]2[CH:9]=[CH:8][C:7]([F:23])=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:25])([F:1])[F:24])[CH:11]=2)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 866460542,2,2-trifluoro-N-{2-fluoro-5-[methyl(5-nitropyridin-2-yl)amino]phenyl}acetamide

Product 1

HCID 86646056N-{5-[(5-aminopyridin-2-yl)(methyl)amino]-2-fluorophenyl}-2,2,2-trifluoroacetamideYield 128.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-{2-fluoro-5-[methyl(5-nitropyridin-2-yl)amino]phenyl}acetamide (18.0 g, 50.2 mmol) in ethanol (100 mL)/tetrahydrofuran (20 mL) was added 10% palladium-carbon (1.8 g), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (1 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to give the title compound (21.2 g, 68%) as colorless crystals.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5b6feb7a01604f30a1496dc8d292b173
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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