Triethylamine → HCID 59750423, compound

HRID 499653Notes

Reaction equation

HRID 499653 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5][N:4]=1)#[N:2].[C:21](OC)(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[SH:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:29]=[C:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[S:24][C:1]([C:3]2[CH:8]=[C:7]([CH:9]3[CH2:13][CH2:12][CH2:11][N:10]3[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5][N:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939435HCID 22939435, compound

Product 1

HCID 59750423HCID 59750423, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 2-(2-cyano-4-pyridyl)-1-pyrrolidinecarboxylate (1.6 g, 6.0 mmol) and methyl thiosalicylate (3.0 g, 18.3 mmol) were dissolved in toluene (10 ml), and triethylamine (5.0 ml, 35.8 mmol) was added thereto. The mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (1:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.5 g, 63%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-hexane (1:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-43871830331a411d834731c91729f5cc
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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