Nicotinamide → HCID 15670246, compound

HRID 1646308Notes

Reaction equation

HRID 1646308 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([O:15][CH2:16][CH2:17]Br)=[O:14])=[O:8])(=[O:3])[CH3:2].N1C=CC=C(C(N)=[O:36])C=1>CO>[C:1]([S:4][CH2:5][CH:6]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([O:15][CH2:16][CH2:17][OH:36])=[O:14])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 936NicotinamideHCID 15670245HCID 15670245, compound

Product 1

HCID 15670246HCID 15670246, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromoethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate (compound of Example 123) (0.63 g) and 3-pyridinecarboxamide (0.17 g) are dissolved in methanol (10 ml), and the mixture is refluxed overnight. Methanol is distilled off under reduced pressure, and the residue is dissolved in ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. Ethyl acetate is distilled off under reduced pressure. The residue is purified by a medium pressure column chromatography with silica gel (eluant, chloroform). The fractions containing the desired compound are collected, and chloroform is distilled off under reduced pressure to give the title compound (0.3 g) as an oily substance.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. distillationMethanol is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate is distilled off under reduced pressure
  7. customThe residue is purified by a medium pressure column chromatography with silica gel (eluant, chloroform)
  8. additionThe fractions containing the desired compound
  9. customare collected
  10. distillationchloroform is distilled off under reduced pressure

Sources & evidence

ORD record
ord-92792967dbca463485f59e48fa8c25b2
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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