Triethylamine → HCID 59750199, compound

HRID 748110Notes

Reaction equation

HRID 748110 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[CH:19]=[CH:18][CH:17]=[C:16]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:20]1([C:16]2[N:15]=[C:14]([C:12]3[S:4][C:3]4[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=4[C:1](=[O:10])[N:13]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939575HCID 22939575, compound

Product 1

HCID 59750199HCID 59750199, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.36 g, 2.1 mmol), 2-cyano-6-(1-piperidinyl)pyridine (0.40 g, 2.1 mmol), triethylamine (0.45 ml, 3.1 mmol) and toluene (50 ml) was refluxed for 48 hrs as described in Example 1. The solvent was concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v). The obtained crystals were recrystallized from hexane-ethyl acetate to give the titled compound (0.08 g, 13%) as crystals.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe solvent was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (2:1
  4. customThe obtained crystals were recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-2b385ceb5d344eca993afc578a967331
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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