Nicotinamide → HCID 15670246, compound

HRID 248701Notes

Reaction equation

HRID 248701 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. IR (film; cm-1): 1715, 1685, 1660 Mass spectrum (SIMS) [M+H]+ : m/z 402

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-9305a07a54fd44da8b109e3b1fe5ddfd
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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