Triethylamine → HCID 59750339, compound

HRID 748459Notes

Reaction equation

HRID 748459 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:4]=1)#[N:2].[C:20](OC)(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[SH:23].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:28]=[C:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[S:23][C:1]([C:3]2[N:4]=[C:5]([CH2:9][O:10][CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 86596472HCID 86596472, compound

Product 1

HCID 59750339HCID 59750339, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 3-[(2-cyano-6-pyridyl)]methoxypropanoate (2.62 g, 10 mmol) and methyl thiosalicylate (1.85 g, 11 mmol) were dissolved in toluene (30 ml), and triethylamine (1.70 ml, 12 mmol) were added thereto. The reaction mixture was refluxed under nitrogen atmosphere for 15 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The titled compound (2.92 g, 71%) was given from the fraction eluted with ethyl acetate-hexane (1:2, v/v) and recrystallized from ethyl acetate-isopropyl ether.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 15 hrs
  2. customThe solvent was evaporated
  3. washeluted with ethyl acetate-hexane (1:2
  4. customv/v) and recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-a2d0832090b1480c9741f64fae5a3b38
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…