Triethylamine → HCID 59750129, compound

HRID 499323Notes

Reaction equation

HRID 499323 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][N:32]=3)[C:28]#[N:29])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[C:27]([C:28]4[S:4][C:3]5[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=5[C:1](=[O:10])[N:29]=4)[CH:30]=[CH:31][N:32]=3)[CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 24699773HCID 24699773, compound

Product 1

HCID 59750129HCID 59750129, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (0.70 g, 4.2 mmol) and 2-[4-(4-fluorophenyl)-1-piperazinyl]isonicotinonitrile (0.69 g, 2.4 mmol) were dissolved in toluene (2.0 ml), and triethylamine (0.71 ml, 5.1 mmol) was added thereto. The reaction mixture was refluxed for 17 hrs and the precipitated crystals were collected by filtration. The filtrate was concentrated, subjected to a silica gel (50 g) column chromatography, eluted with hexane-ethyl acetate (2:1, v/v) to give crystals, which were combined with the previously obtained crystals and recrystallized from acetone-ethanol to give the titled compound (0.18 g, 17%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hrs
  2. filtrationthe precipitated crystals were collected by filtration
  3. concentrationThe filtrate was concentrated
  4. washeluted with hexane-ethyl acetate (2:1
  5. customv/v) to give crystals, which
  6. customrecrystallized from acetone-ethanol

Sources & evidence

ORD record
ord-6dce85708e04476893ebd0f6820c42cb
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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