1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide

HRID 2247285Notes

Reaction equation

HRID 2247285 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.[C:12](NC1C=CC=CC=1)([CH3:15])([CH3:14])[CH3:13].[CH:23]1[CH:24]=[CH:25][C:26]2[N:31](O)N=N[C:27]=2[CH:28]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:12]([C:23]1[CH:28]=[CH:27][C:26]([NH:31][C:8](=[O:10])[C:7]2[CH:6]=[CH:5][C:4]([F:11])=[N:3][C:2]=2[F:1])=[CH:25][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 105830702,6-Difluoropyridine-3-carboxylic acid

Product 1

HCID 22249203N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-difluoropyridine-3-carboxylic acid (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h. The mixture was washed with aq. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product.

Workup

  1. washThe mixture was washed with aq. NaHCO3 and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via flash chromatography on silica (Hex:EtOAc=4:1)

Sources & evidence

ORD record
ord-cc222905c57747529d0ffe3f78a68d3c
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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