Pyridine → HCID 58788290, compound

HRID 2374743Notes

Reaction equation

HRID 2374743 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11](O)=O.C(Cl)(=O)C(Cl)=O.[CH2:20]([O:22][C:23](=[O:35])[CH2:24][NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32](=[O:34])[NH2:33])[CH3:21].N1C=CC=CC=1>ClCCl.CN(C=O)C.C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:25]([CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:35])[C:26]2[C:27]([C:32](=[O:34])[N:33]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2

Participants

9

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 37993363-(2,3-difluorophenyl)propanoic AcidHCID 13566148HCID 13566148, compound

Product 1

HCID 58788290HCID 58788290, compoundYield 82.4%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2,3-difluorophenyl)-propionic acid (Int. A1) (5 g, 26.9 mmol) in anhydrous dichloromethane (50 ml) containing a few drops of DMF was added oxalyl chloride (4.7 ml, 53.8 mmol) at 0° C. under argon. The solution was then stirred at ambient temperature for 2 h and the solvent removed in vacuo. The residue which contained the acid chloride (Int. A54) was dissoved in toluene (50 ml) and added to a slurry of (2-carbamoylphenylamino)-acetic acid ethyl ester (5.0 g, 22.5 mmol) in toluene (50 ml) containing pyridine (1 ml) and 4-dimethylaminopyridine (DMAP) (100 mg). After 16 h at 90° C. the solvent was evaporated and the solid residue washed with water, aqueous ammonia and ether to give the title compound (6.9 g, 82%) as a cream solid. 1H-NMR (DMSO) δ 1.24 (3H, t), 3.13 (2H, t), 3.34 (2H, m), 4.24 (2H, q), 5.48 (2H, s), 7.19 (1H, m), 7.29-7.35 (2H, m), 7.60-7.72 (2H, m), 7.94 (1H, t), 8.19 (1H, d); MS (APCI+) found (M+1)=373; C20H18F2N2O3 requires 372.

Workup

  1. customthe solvent removed in vacuo
  2. customAfter 16 h at 90° C. the solvent was evaporated
  3. washthe solid residue washed with water, aqueous ammonia and ether

Sources & evidence

ORD record
ord-5972bf1da0194e1abea177507f1b399a
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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