Triethylamine → HCID 59750251, compound

HRID 499310Notes

Reaction equation

HRID 499310 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:12]([C:14]1[N:19]=[C:18]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:17]=[CH:16][CH:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:10]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:12]([C:14]2[N:19]=[C:18]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:17]=[CH:16][CH:15]=2)=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939521HCID 22939521, compound

Product 1

HCID 59750251HCID 59750251, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (1.0 g, 6.1 mmol) and tert-butyl 3-[3-(6-cyano-2-pyridyl)propoxy]propanoate (1.6 g, 5.5 mmol) were dissolved in toluene (5.0 ml). Triethylamine (1.35 ml, 9.7 mmol) was added to the mixture and the mixture was refluxed for 14 hrs. The reaction mixture was subjected to a silica gel (110 g) column chromatography and eluted with hexane-ethyl acetate (3:2, v/v) to give the titled compound (1.7 g, 67%) as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 14 hrs
  2. washeluted with hexane-ethyl acetate (3:2

Sources & evidence

ORD record
ord-1c10e0e86436456792185e4bf95edbe6
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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