Triethylamine → HCID 59750258, compound

HRID 499319Notes

Reaction equation

HRID 499319 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([NH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][N:26]=1)[C:22]#[N:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([NH:18][C:19]1[CH:20]=[C:21]([C:22]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:23]=2)[CH:24]=[CH:25][N:26]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 229392754-Pyridinecarbonitrile, 2-(hexylamino)-

Product 1

HCID 59750258HCID 59750258, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiosalicylate (0.44 g, 2.6 mmol) and 2-(hexylamino)isonicotinonitrile (0.26 g, 1.3 mmol) were dissolved in toluene (2.0 ml), and triethylamine (0.40 ml, 2.9 mmol) was added thereto. The reaction mixture was refluxed for 14 hrs, subjected to a silica gel (50 g) chromatography, eluted with hexane-ethyl acetate (2:1, v/v) and recrystallized from ethanol to give the titled compound (0.08 g, 18%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 14 hrs
  2. washeluted with hexane-ethyl acetate (2:1
  3. customv/v) and recrystallized from ethanol

Sources & evidence

ORD record
ord-9792ba0608d5483ba25f45a868f29704
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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