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

HRID 1800636Notes

Reaction equation

HRID 1800636 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 under a hydrogen atmosphere (1 atm) at room temperature for 14 hr. 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-bf1adad9e9fd4ecc83c0f37bc9d67dd8
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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