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

HRID 2212720Notes

Reaction equation

HRID 2212720 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.F[C:13]1[C:18]([C:19](O)=O)=[CH:17]C=CN=1.C([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[C:7]([C:8]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([C:18]([CH3:19])([CH3:13])[CH3:17])=[CH:31][CH:32]=2)=[O:10])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 960892-Fluoronicotinic acidHCID 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 (prepared similar to that described for 2-fluoropyridine-3-carboxylic acid, Example 64) (3.2 g, 20 mmol), t-butylaniline 11 (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmole), 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 the 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-5f92ff36deba46d19f0bfbe2eeba7ca8
Source dataset
uspto-grants-2006_09
Patent number
US07102009B2

Reaction notes

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