Picolinic acid → HCID 67168545, compound

HRID 872838Notes

Reaction equation

HRID 872838 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][NH2:9])=[CH:4][CH:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](O)=[O:24].CCN=C=NCCCN(C)C>C1COCC1>[Br:1][C:2]1[O:6][C:5]([CH:7]([S:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:8][NH:9][C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=2)=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67168460HCID 67168460, compound

Product 1

HCID 67168545HCID 67168545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(5-Bromofuran-2-yl)-2-phenylsulfanylethylamine (0.28 g, 0.0009389 mol), 2-pyridinecarboxylic acid (0.12 g, 0.001005 mol) and EDCI were stirred in dry THF (10 ml). After disappearing of the starting material the solvent was evaporated. Then chloroform was added and the solution was washed with 1 M Na2CO3 and water, dried with Na2SO4 and evaporated. The crude product was purified by flash chromatography using heptane-EtOAc as a gradient eluent (85:15-70:30). 1H NMR (400 MHz, DMSO-d6): 3.75-3.80 (2H, m), 4.78-4.84 (1H, m), 6.33-6.37 (2H, m), 6.44 (1H, d), 7.26-7.40 (4H, m), 7.59-7.62 (1H, m), 7.97-8.04 (2H, m), 8.62-8.64 (1H, m), 9.08 (1H, m).

Workup

  1. customwas evaporated
  2. additionThen chloroform was added
  3. washthe solution was washed with 1 M Na2CO3 and water
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-deb2966bf6414da4aa3ad468914d1b98
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…